diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 7cde9314450eb..25a34b894cd59 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -24887,12 +24887,17 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
 
     // This like getBaseTypeOfLiteralType, but instead treats enum literals as strings/numbers instead
     // of returning their enum base type (which depends on the types of other literals in the enum).
-    function getBaseTypeOfLiteralTypeForComparison(type: Type): Type {
-        return type.flags & (TypeFlags.StringLiteral | TypeFlags.TemplateLiteral | TypeFlags.StringMapping) ? stringType :
+    // It also checks if the type used in the comparison may be undefined or null (or is unknown/unconstrained)
+    function getBaseTypeForComparison(type: Type): Type {
+        return type.flags & TypeFlags.Instantiable && strictNullChecks ? getBaseConstraintOfType(type) ?? unknownUnionType :
+            type.flags & (TypeFlags.StringLiteral | TypeFlags.TemplateLiteral | TypeFlags.StringMapping) ? stringType :
             type.flags & (TypeFlags.NumberLiteral | TypeFlags.Enum) ? numberType :
             type.flags & TypeFlags.BigIntLiteral ? bigintType :
             type.flags & TypeFlags.BooleanLiteral ? booleanType :
-            type.flags & TypeFlags.Union ? mapType(type, getBaseTypeOfLiteralTypeForComparison) :
+            type.flags & TypeFlags.Union ? mapType(type, getBaseTypeForComparison) :
+            type.flags & TypeFlags.Intersection && every((type as IntersectionType).types, t => {
+                    return getBaseTypeForComparison(t) === unknownUnionType;
+                }) ? unknownUnionType :
             type;
     }
 
@@ -39677,8 +39682,8 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             case SyntaxKind.LessThanEqualsToken:
             case SyntaxKind.GreaterThanEqualsToken:
                 if (checkForDisallowedESSymbolOperand(operator)) {
-                    leftType = getBaseTypeOfLiteralTypeForComparison(checkNonNullType(leftType, left));
-                    rightType = getBaseTypeOfLiteralTypeForComparison(checkNonNullType(rightType, right));
+                    leftType = checkNonNullType(getBaseTypeForComparison(leftType), left);
+                    rightType = checkNonNullType(getBaseTypeForComparison(rightType), right);
                     reportOperatorErrorUnless((left, right) => {
                         if (isTypeAny(left) || isTypeAny(right)) {
                             return true;
diff --git a/tests/baselines/reference/unconstrainedTypeComparison.errors.txt b/tests/baselines/reference/unconstrainedTypeComparison.errors.txt
new file mode 100644
index 0000000000000..445c740f60d6a
--- /dev/null
+++ b/tests/baselines/reference/unconstrainedTypeComparison.errors.txt
@@ -0,0 +1,185 @@
+unconstrainedTypeComparison.ts(2,12): error TS18049: 'a' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(2,16): error TS18049: 'b' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(6,12): error TS18049: 'a' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(6,16): error TS18049: 'b' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(10,12): error TS18046: 'a' is of type 'unknown'.
+unconstrainedTypeComparison.ts(10,16): error TS18046: 'b' is of type 'unknown'.
+unconstrainedTypeComparison.ts(14,12): error TS18049: 'a' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(14,16): error TS18049: 'b' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(18,12): error TS18049: 'a' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(18,16): error TS18049: 'b' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(22,12): error TS18046: 'a' is of type 'unknown'.
+unconstrainedTypeComparison.ts(22,16): error TS18046: 'b' is of type 'unknown'.
+unconstrainedTypeComparison.ts(26,12): error TS18048: 'a' is possibly 'undefined'.
+unconstrainedTypeComparison.ts(26,16): error TS18048: 'b' is possibly 'undefined'.
+unconstrainedTypeComparison.ts(30,12): error TS18047: 'a' is possibly 'null'.
+unconstrainedTypeComparison.ts(30,16): error TS18047: 'b' is possibly 'null'.
+unconstrainedTypeComparison.ts(34,12): error TS18049: 'a' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(34,16): error TS18049: 'b' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(38,12): error TS18049: 'x' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(38,16): error TS18049: 'y' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(42,12): error TS18049: 'x' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(42,16): error TS18049: 'y' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(49,12): error TS18047: 'x' is possibly 'null'.
+unconstrainedTypeComparison.ts(49,16): error TS18049: 'y' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(56,12): error TS18047: 'x' is possibly 'null'.
+unconstrainedTypeComparison.ts(56,16): error TS18049: 'y' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(60,12): error TS18049: 'x' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(60,16): error TS18049: 'y' is possibly 'null' or 'undefined'.
+unconstrainedTypeComparison.ts(74,12): error TS18047: 'x' is possibly 'null'.
+unconstrainedTypeComparison.ts(74,16): error TS18048: 'y' is possibly 'undefined'.
+unconstrainedTypeComparison.ts(85,12): error TS18047: 'a' is possibly 'null'.
+unconstrainedTypeComparison.ts(85,16): error TS18048: 'b' is possibly 'undefined'.
+
+
+==== unconstrainedTypeComparison.ts (32 errors) ====
+    function f1<T>(a: T, b: T): boolean {
+        return a > b;
+               ~
+!!! error TS18049: 'a' is possibly 'null' or 'undefined'.
+                   ~
+!!! error TS18049: 'b' is possibly 'null' or 'undefined'.
+    }
+    
+    function f2<T extends {} | undefined | null>(a: T, b: T): boolean {
+        return a > b;
+               ~
+!!! error TS18049: 'a' is possibly 'null' or 'undefined'.
+                   ~
+!!! error TS18049: 'b' is possibly 'null' or 'undefined'.
+    }
+    
+    function f3<T extends unknown>(a: T, b: T): boolean {
+        return a > b;
+               ~
+!!! error TS18046: 'a' is of type 'unknown'.
+                   ~
+!!! error TS18046: 'b' is of type 'unknown'.
+    }
+    
+    function f4<T, U extends T>(a: U, b: U): boolean {
+        return a > b;
+               ~
+!!! error TS18049: 'a' is possibly 'null' or 'undefined'.
+                   ~
+!!! error TS18049: 'b' is possibly 'null' or 'undefined'.
+    }
+    
+    function f5<T extends {} | undefined | null, U extends T>(a: U, b: U): boolean {
+        return a > b;
+               ~
+!!! error TS18049: 'a' is possibly 'null' or 'undefined'.
+                   ~
+!!! error TS18049: 'b' is possibly 'null' or 'undefined'.
+    }
+    
+    function f6<T extends unknown, U extends T>(a: U, b: U): boolean {
+        return a > b;
+               ~
+!!! error TS18046: 'a' is of type 'unknown'.
+                   ~
+!!! error TS18046: 'b' is of type 'unknown'.
+    }
+    
+    function f7<T extends {} | undefined, U extends T>(a: U, b: U): boolean {
+        return a > b;
+               ~
+!!! error TS18048: 'a' is possibly 'undefined'.
+                   ~
+!!! error TS18048: 'b' is possibly 'undefined'.
+    }
+    
+    function f8<T extends {} | null, U extends T>(a: U, b: U): boolean {
+        return a > b;
+               ~
+!!! error TS18047: 'a' is possibly 'null'.
+                   ~
+!!! error TS18047: 'b' is possibly 'null'.
+    }
+    
+    function f9<T extends undefined | null, U extends T>(a: U, b: U): boolean {
+        return a > b;
+               ~
+!!! error TS18049: 'a' is possibly 'null' or 'undefined'.
+                   ~
+!!! error TS18049: 'b' is possibly 'null' or 'undefined'.
+    }
+    
+    function f10<T, U>(x: T | U, y: T | U) {
+        return x < y;
+               ~
+!!! error TS18049: 'x' is possibly 'null' or 'undefined'.
+                   ~
+!!! error TS18049: 'y' is possibly 'null' or 'undefined'.
+    }
+    
+    function f11<T, U extends T>(x: T | number, y: U | number) {
+        return x < y;
+               ~
+!!! error TS18049: 'x' is possibly 'null' or 'undefined'.
+                   ~
+!!! error TS18049: 'y' is possibly 'null' or 'undefined'.
+    }
+    
+    function f12<T, U extends T>(x: T | number, y: U | number) {
+        if (x === undefined) {
+            return false;
+        }
+        return x < y;
+               ~
+!!! error TS18047: 'x' is possibly 'null'.
+                   ~
+!!! error TS18049: 'y' is possibly 'null' or 'undefined'.
+    }
+    
+    function f13<T, U extends T | number>(x: U, y: U) {
+        if (x === undefined) {
+            return false;
+        }
+        return x < y;
+               ~
+!!! error TS18047: 'x' is possibly 'null'.
+                   ~
+!!! error TS18049: 'y' is possibly 'null' or 'undefined'.
+    }
+    
+    function f14<T, U>(x: T & U, y: T & U) {
+        return x < y;
+               ~
+!!! error TS18049: 'x' is possibly 'null' or 'undefined'.
+                   ~
+!!! error TS18049: 'y' is possibly 'null' or 'undefined'.
+    }
+    
+    function f15<T, U extends T>(x: T & number, y: U & number) {
+        return x < y;
+    }
+    
+    function f16<T, U extends T>(x: T & U, y: U) {
+        if (x === undefined) {
+            return false;
+        }
+        if (y === null) {
+            return false;
+        }
+        return x < y;
+               ~
+!!! error TS18047: 'x' is possibly 'null'.
+                   ~
+!!! error TS18048: 'y' is possibly 'undefined'.
+    }
+    
+    
+    function compare<T>(a: T, b: T): boolean {
+        if (a === undefined) {
+            return false;
+        }
+        if (b === null) {
+            return false;
+        }
+        return a > b;
+               ~
+!!! error TS18047: 'a' is possibly 'null'.
+                   ~
+!!! error TS18048: 'b' is possibly 'undefined'.
+    }
\ No newline at end of file
diff --git a/tests/baselines/reference/unconstrainedTypeComparison.symbols b/tests/baselines/reference/unconstrainedTypeComparison.symbols
new file mode 100644
index 0000000000000..0a8a9a7a30d26
--- /dev/null
+++ b/tests/baselines/reference/unconstrainedTypeComparison.symbols
@@ -0,0 +1,287 @@
+//// [tests/cases/compiler/unconstrainedTypeComparison.ts] ////
+
+=== unconstrainedTypeComparison.ts ===
+function f1<T>(a: T, b: T): boolean {
+>f1 : Symbol(f1, Decl(unconstrainedTypeComparison.ts, 0, 0))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 0, 12))
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 0, 15))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 0, 12))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 0, 20))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 0, 12))
+
+    return a > b;
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 0, 15))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 0, 20))
+}
+
+function f2<T extends {} | undefined | null>(a: T, b: T): boolean {
+>f2 : Symbol(f2, Decl(unconstrainedTypeComparison.ts, 2, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 4, 12))
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 4, 45))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 4, 12))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 4, 50))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 4, 12))
+
+    return a > b;
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 4, 45))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 4, 50))
+}
+
+function f3<T extends unknown>(a: T, b: T): boolean {
+>f3 : Symbol(f3, Decl(unconstrainedTypeComparison.ts, 6, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 8, 12))
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 8, 31))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 8, 12))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 8, 36))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 8, 12))
+
+    return a > b;
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 8, 31))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 8, 36))
+}
+
+function f4<T, U extends T>(a: U, b: U): boolean {
+>f4 : Symbol(f4, Decl(unconstrainedTypeComparison.ts, 10, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 12, 12))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 12, 14))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 12, 12))
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 12, 28))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 12, 14))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 12, 33))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 12, 14))
+
+    return a > b;
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 12, 28))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 12, 33))
+}
+
+function f5<T extends {} | undefined | null, U extends T>(a: U, b: U): boolean {
+>f5 : Symbol(f5, Decl(unconstrainedTypeComparison.ts, 14, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 16, 12))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 16, 44))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 16, 12))
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 16, 58))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 16, 44))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 16, 63))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 16, 44))
+
+    return a > b;
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 16, 58))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 16, 63))
+}
+
+function f6<T extends unknown, U extends T>(a: U, b: U): boolean {
+>f6 : Symbol(f6, Decl(unconstrainedTypeComparison.ts, 18, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 20, 12))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 20, 30))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 20, 12))
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 20, 44))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 20, 30))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 20, 49))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 20, 30))
+
+    return a > b;
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 20, 44))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 20, 49))
+}
+
+function f7<T extends {} | undefined, U extends T>(a: U, b: U): boolean {
+>f7 : Symbol(f7, Decl(unconstrainedTypeComparison.ts, 22, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 24, 12))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 24, 37))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 24, 12))
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 24, 51))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 24, 37))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 24, 56))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 24, 37))
+
+    return a > b;
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 24, 51))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 24, 56))
+}
+
+function f8<T extends {} | null, U extends T>(a: U, b: U): boolean {
+>f8 : Symbol(f8, Decl(unconstrainedTypeComparison.ts, 26, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 28, 12))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 28, 32))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 28, 12))
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 28, 46))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 28, 32))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 28, 51))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 28, 32))
+
+    return a > b;
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 28, 46))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 28, 51))
+}
+
+function f9<T extends undefined | null, U extends T>(a: U, b: U): boolean {
+>f9 : Symbol(f9, Decl(unconstrainedTypeComparison.ts, 30, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 32, 12))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 32, 39))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 32, 12))
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 32, 53))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 32, 39))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 32, 58))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 32, 39))
+
+    return a > b;
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 32, 53))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 32, 58))
+}
+
+function f10<T, U>(x: T | U, y: T | U) {
+>f10 : Symbol(f10, Decl(unconstrainedTypeComparison.ts, 34, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 36, 13))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 36, 15))
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 36, 19))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 36, 13))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 36, 15))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 36, 28))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 36, 13))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 36, 15))
+
+    return x < y;
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 36, 19))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 36, 28))
+}
+
+function f11<T, U extends T>(x: T | number, y: U | number) {
+>f11 : Symbol(f11, Decl(unconstrainedTypeComparison.ts, 38, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 40, 13))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 40, 15))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 40, 13))
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 40, 29))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 40, 13))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 40, 43))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 40, 15))
+
+    return x < y;
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 40, 29))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 40, 43))
+}
+
+function f12<T, U extends T>(x: T | number, y: U | number) {
+>f12 : Symbol(f12, Decl(unconstrainedTypeComparison.ts, 42, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 44, 13))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 44, 15))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 44, 13))
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 44, 29))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 44, 13))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 44, 43))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 44, 15))
+
+    if (x === undefined) {
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 44, 29))
+>undefined : Symbol(undefined)
+
+        return false;
+    }
+    return x < y;
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 44, 29))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 44, 43))
+}
+
+function f13<T, U extends T | number>(x: U, y: U) {
+>f13 : Symbol(f13, Decl(unconstrainedTypeComparison.ts, 49, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 51, 13))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 51, 15))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 51, 13))
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 51, 38))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 51, 15))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 51, 43))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 51, 15))
+
+    if (x === undefined) {
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 51, 38))
+>undefined : Symbol(undefined)
+
+        return false;
+    }
+    return x < y;
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 51, 38))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 51, 43))
+}
+
+function f14<T, U>(x: T & U, y: T & U) {
+>f14 : Symbol(f14, Decl(unconstrainedTypeComparison.ts, 56, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 58, 13))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 58, 15))
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 58, 19))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 58, 13))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 58, 15))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 58, 28))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 58, 13))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 58, 15))
+
+    return x < y;
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 58, 19))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 58, 28))
+}
+
+function f15<T, U extends T>(x: T & number, y: U & number) {
+>f15 : Symbol(f15, Decl(unconstrainedTypeComparison.ts, 60, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 62, 13))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 62, 15))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 62, 13))
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 62, 29))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 62, 13))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 62, 43))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 62, 15))
+
+    return x < y;
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 62, 29))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 62, 43))
+}
+
+function f16<T, U extends T>(x: T & U, y: U) {
+>f16 : Symbol(f16, Decl(unconstrainedTypeComparison.ts, 64, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 66, 13))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 66, 15))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 66, 13))
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 66, 29))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 66, 13))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 66, 15))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 66, 38))
+>U : Symbol(U, Decl(unconstrainedTypeComparison.ts, 66, 15))
+
+    if (x === undefined) {
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 66, 29))
+>undefined : Symbol(undefined)
+
+        return false;
+    }
+    if (y === null) {
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 66, 38))
+
+        return false;
+    }
+    return x < y;
+>x : Symbol(x, Decl(unconstrainedTypeComparison.ts, 66, 29))
+>y : Symbol(y, Decl(unconstrainedTypeComparison.ts, 66, 38))
+}
+
+
+function compare<T>(a: T, b: T): boolean {
+>compare : Symbol(compare, Decl(unconstrainedTypeComparison.ts, 74, 1))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 77, 17))
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 77, 20))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 77, 17))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 77, 25))
+>T : Symbol(T, Decl(unconstrainedTypeComparison.ts, 77, 17))
+
+    if (a === undefined) {
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 77, 20))
+>undefined : Symbol(undefined)
+
+        return false;
+    }
+    if (b === null) {
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 77, 25))
+
+        return false;
+    }
+    return a > b;
+>a : Symbol(a, Decl(unconstrainedTypeComparison.ts, 77, 20))
+>b : Symbol(b, Decl(unconstrainedTypeComparison.ts, 77, 25))
+}
diff --git a/tests/baselines/reference/unconstrainedTypeComparison.types b/tests/baselines/reference/unconstrainedTypeComparison.types
new file mode 100644
index 0000000000000..8f3808ddb7cad
--- /dev/null
+++ b/tests/baselines/reference/unconstrainedTypeComparison.types
@@ -0,0 +1,360 @@
+//// [tests/cases/compiler/unconstrainedTypeComparison.ts] ////
+
+=== unconstrainedTypeComparison.ts ===
+function f1<T>(a: T, b: T): boolean {
+>f1 : <T>(a: T, b: T) => boolean
+>   : ^ ^^ ^^ ^^ ^^ ^^^^^       
+>a : T
+>  : ^
+>b : T
+>  : ^
+
+    return a > b;
+>a > b : boolean
+>      : ^^^^^^^
+>a : T
+>  : ^
+>b : T
+>  : ^
+}
+
+function f2<T extends {} | undefined | null>(a: T, b: T): boolean {
+>f2 : <T extends {} | undefined | null>(a: T, b: T) => boolean
+>   : ^ ^^^^^^^^^                     ^^ ^^ ^^ ^^ ^^^^^       
+>a : T
+>  : ^
+>b : T
+>  : ^
+
+    return a > b;
+>a > b : boolean
+>      : ^^^^^^^
+>a : T
+>  : ^
+>b : T
+>  : ^
+}
+
+function f3<T extends unknown>(a: T, b: T): boolean {
+>f3 : <T extends unknown>(a: T, b: T) => boolean
+>   : ^ ^^^^^^^^^       ^^ ^^ ^^ ^^ ^^^^^       
+>a : T
+>  : ^
+>b : T
+>  : ^
+
+    return a > b;
+>a > b : boolean
+>      : ^^^^^^^
+>a : T
+>  : ^
+>b : T
+>  : ^
+}
+
+function f4<T, U extends T>(a: U, b: U): boolean {
+>f4 : <T, U extends T>(a: U, b: U) => boolean
+>   : ^ ^^ ^^^^^^^^^ ^^ ^^ ^^ ^^ ^^^^^       
+>a : U
+>  : ^
+>b : U
+>  : ^
+
+    return a > b;
+>a > b : boolean
+>      : ^^^^^^^
+>a : U
+>  : ^
+>b : U
+>  : ^
+}
+
+function f5<T extends {} | undefined | null, U extends T>(a: U, b: U): boolean {
+>f5 : <T extends {} | undefined | null, U extends T>(a: U, b: U) => boolean
+>   : ^ ^^^^^^^^^                     ^^ ^^^^^^^^^ ^^ ^^ ^^ ^^ ^^^^^       
+>a : U
+>  : ^
+>b : U
+>  : ^
+
+    return a > b;
+>a > b : boolean
+>      : ^^^^^^^
+>a : U
+>  : ^
+>b : U
+>  : ^
+}
+
+function f6<T extends unknown, U extends T>(a: U, b: U): boolean {
+>f6 : <T extends unknown, U extends T>(a: U, b: U) => boolean
+>   : ^ ^^^^^^^^^       ^^ ^^^^^^^^^ ^^ ^^ ^^ ^^ ^^^^^       
+>a : U
+>  : ^
+>b : U
+>  : ^
+
+    return a > b;
+>a > b : boolean
+>      : ^^^^^^^
+>a : U
+>  : ^
+>b : U
+>  : ^
+}
+
+function f7<T extends {} | undefined, U extends T>(a: U, b: U): boolean {
+>f7 : <T extends {} | undefined, U extends T>(a: U, b: U) => boolean
+>   : ^ ^^^^^^^^^              ^^ ^^^^^^^^^ ^^ ^^ ^^ ^^ ^^^^^       
+>a : U
+>  : ^
+>b : U
+>  : ^
+
+    return a > b;
+>a > b : boolean
+>      : ^^^^^^^
+>a : U
+>  : ^
+>b : U
+>  : ^
+}
+
+function f8<T extends {} | null, U extends T>(a: U, b: U): boolean {
+>f8 : <T extends {} | null, U extends T>(a: U, b: U) => boolean
+>   : ^ ^^^^^^^^^         ^^ ^^^^^^^^^ ^^ ^^ ^^ ^^ ^^^^^       
+>a : U
+>  : ^
+>b : U
+>  : ^
+
+    return a > b;
+>a > b : boolean
+>      : ^^^^^^^
+>a : U
+>  : ^
+>b : U
+>  : ^
+}
+
+function f9<T extends undefined | null, U extends T>(a: U, b: U): boolean {
+>f9 : <T extends undefined | null, U extends T>(a: U, b: U) => boolean
+>   : ^ ^^^^^^^^^                ^^ ^^^^^^^^^ ^^ ^^ ^^ ^^ ^^^^^       
+>a : U
+>  : ^
+>b : U
+>  : ^
+
+    return a > b;
+>a > b : boolean
+>      : ^^^^^^^
+>a : U
+>  : ^
+>b : U
+>  : ^
+}
+
+function f10<T, U>(x: T | U, y: T | U) {
+>f10 : <T, U>(x: T | U, y: T | U) => boolean
+>    : ^ ^^ ^^ ^^     ^^ ^^     ^^^^^^^^^^^^
+>x : T | U
+>  : ^^^^^
+>y : T | U
+>  : ^^^^^
+
+    return x < y;
+>x < y : boolean
+>      : ^^^^^^^
+>x : T | U
+>  : ^^^^^
+>y : T | U
+>  : ^^^^^
+}
+
+function f11<T, U extends T>(x: T | number, y: U | number) {
+>f11 : <T, U extends T>(x: T | number, y: U | number) => boolean
+>    : ^ ^^ ^^^^^^^^^ ^^ ^^          ^^ ^^          ^^^^^^^^^^^^
+>x : number | T
+>  : ^^^^^^^^^^
+>y : number | U
+>  : ^^^^^^^^^^
+
+    return x < y;
+>x < y : boolean
+>      : ^^^^^^^
+>x : number | T
+>  : ^^^^^^^^^^
+>y : number | U
+>  : ^^^^^^^^^^
+}
+
+function f12<T, U extends T>(x: T | number, y: U | number) {
+>f12 : <T, U extends T>(x: T | number, y: U | number) => boolean
+>    : ^ ^^ ^^^^^^^^^ ^^ ^^          ^^ ^^          ^^^^^^^^^^^^
+>x : number | T
+>  : ^^^^^^^^^^
+>y : number | U
+>  : ^^^^^^^^^^
+
+    if (x === undefined) {
+>x === undefined : boolean
+>                : ^^^^^^^
+>x : number | T
+>  : ^^^^^^^^^^
+>undefined : undefined
+>          : ^^^^^^^^^
+
+        return false;
+>false : false
+>      : ^^^^^
+    }
+    return x < y;
+>x < y : boolean
+>      : ^^^^^^^
+>x : number | (T & ({} | null))
+>  : ^^^^^^^^^^^^^^^^^^^^^^^^^^
+>y : number | U
+>  : ^^^^^^^^^^
+}
+
+function f13<T, U extends T | number>(x: U, y: U) {
+>f13 : <T, U extends T | number>(x: U, y: U) => boolean
+>    : ^ ^^ ^^^^^^^^^          ^^ ^^ ^^ ^^ ^^^^^^^^^^^^
+>x : U
+>  : ^
+>y : U
+>  : ^
+
+    if (x === undefined) {
+>x === undefined : boolean
+>                : ^^^^^^^
+>x : U
+>  : ^
+>undefined : undefined
+>          : ^^^^^^^^^
+
+        return false;
+>false : false
+>      : ^^^^^
+    }
+    return x < y;
+>x < y : boolean
+>      : ^^^^^^^
+>x : U & ({} | null)
+>  : ^^^^^^^^^^^^^^^
+>y : U
+>  : ^
+}
+
+function f14<T, U>(x: T & U, y: T & U) {
+>f14 : <T, U>(x: T & U, y: T & U) => boolean
+>    : ^ ^^ ^^ ^^     ^^ ^^     ^^^^^^^^^^^^
+>x : T & U
+>  : ^^^^^
+>y : T & U
+>  : ^^^^^
+
+    return x < y;
+>x < y : boolean
+>      : ^^^^^^^
+>x : T & U
+>  : ^^^^^
+>y : T & U
+>  : ^^^^^
+}
+
+function f15<T, U extends T>(x: T & number, y: U & number) {
+>f15 : <T, U extends T>(x: T & number, y: U & number) => boolean
+>    : ^ ^^ ^^^^^^^^^ ^^ ^^          ^^ ^^          ^^^^^^^^^^^^
+>x : T & number
+>  : ^^^^^^^^^^
+>y : U & number
+>  : ^^^^^^^^^^
+
+    return x < y;
+>x < y : boolean
+>      : ^^^^^^^
+>x : T & number
+>  : ^^^^^^^^^^
+>y : U & number
+>  : ^^^^^^^^^^
+}
+
+function f16<T, U extends T>(x: T & U, y: U) {
+>f16 : <T, U extends T>(x: T & U, y: U) => boolean
+>    : ^ ^^ ^^^^^^^^^ ^^ ^^     ^^ ^^ ^^^^^^^^^^^^
+>x : T & U
+>  : ^^^^^
+>y : U
+>  : ^
+
+    if (x === undefined) {
+>x === undefined : boolean
+>                : ^^^^^^^
+>x : T & U
+>  : ^^^^^
+>undefined : undefined
+>          : ^^^^^^^^^
+
+        return false;
+>false : false
+>      : ^^^^^
+    }
+    if (y === null) {
+>y === null : boolean
+>           : ^^^^^^^
+>y : U
+>  : ^
+
+        return false;
+>false : false
+>      : ^^^^^
+    }
+    return x < y;
+>x < y : boolean
+>      : ^^^^^^^
+>x : T & U & ({} | null)
+>  : ^^^^^^^^^^^^^^^^^^^
+>y : U & ({} | undefined)
+>  : ^^^^^^^^^^^^^^^^^^^^
+}
+
+
+function compare<T>(a: T, b: T): boolean {
+>compare : <T>(a: T, b: T) => boolean
+>        : ^ ^^ ^^ ^^ ^^ ^^^^^       
+>a : T
+>  : ^
+>b : T
+>  : ^
+
+    if (a === undefined) {
+>a === undefined : boolean
+>                : ^^^^^^^
+>a : T
+>  : ^
+>undefined : undefined
+>          : ^^^^^^^^^
+
+        return false;
+>false : false
+>      : ^^^^^
+    }
+    if (b === null) {
+>b === null : boolean
+>           : ^^^^^^^
+>b : T
+>  : ^
+
+        return false;
+>false : false
+>      : ^^^^^
+    }
+    return a > b;
+>a > b : boolean
+>      : ^^^^^^^
+>a : T & ({} | null)
+>  : ^^^^^^^^^^^^^^^
+>b : T & ({} | undefined)
+>  : ^^^^^^^^^^^^^^^^^^^^
+}
diff --git a/tests/cases/compiler/unconstrainedTypeComparison.ts b/tests/cases/compiler/unconstrainedTypeComparison.ts
new file mode 100644
index 0000000000000..ad69988741917
--- /dev/null
+++ b/tests/cases/compiler/unconstrainedTypeComparison.ts
@@ -0,0 +1,90 @@
+
+// @strict: true
+// @noemit: true
+
+function f1<T>(a: T, b: T): boolean {
+    return a > b;
+}
+
+function f2<T extends {} | undefined | null>(a: T, b: T): boolean {
+    return a > b;
+}
+
+function f3<T extends unknown>(a: T, b: T): boolean {
+    return a > b;
+}
+
+function f4<T, U extends T>(a: U, b: U): boolean {
+    return a > b;
+}
+
+function f5<T extends {} | undefined | null, U extends T>(a: U, b: U): boolean {
+    return a > b;
+}
+
+function f6<T extends unknown, U extends T>(a: U, b: U): boolean {
+    return a > b;
+}
+
+function f7<T extends {} | undefined, U extends T>(a: U, b: U): boolean {
+    return a > b;
+}
+
+function f8<T extends {} | null, U extends T>(a: U, b: U): boolean {
+    return a > b;
+}
+
+function f9<T extends undefined | null, U extends T>(a: U, b: U): boolean {
+    return a > b;
+}
+
+function f10<T, U>(x: T | U, y: T | U) {
+    return x < y;
+}
+
+function f11<T, U extends T>(x: T | number, y: U | number) {
+    return x < y;
+}
+
+function f12<T, U extends T>(x: T | number, y: U | number) {
+    if (x === undefined) {
+        return false;
+    }
+    return x < y;
+}
+
+function f13<T, U extends T | number>(x: U, y: U) {
+    if (x === undefined) {
+        return false;
+    }
+    return x < y;
+}
+
+function f14<T, U>(x: T & U, y: T & U) {
+    return x < y;
+}
+
+function f15<T, U extends T>(x: T & number, y: U & number) {
+    return x < y;
+}
+
+function f16<T, U extends T>(x: T & U, y: U) {
+    if (x === undefined) {
+        return false;
+    }
+    if (y === null) {
+        return false;
+    }
+    return x < y;
+}
+
+
+function compare<T>(a: T, b: T): boolean {
+    if (a === undefined) {
+        return false;
+    }
+    if (b === null) {
+        return false;
+    }
+    return a > b;
+}
\ No newline at end of file