diff --git a/src/main/java/com/back/catchmate/domain/board/converter/BoardConverter.java b/src/main/java/com/back/catchmate/domain/board/converter/BoardConverter.java
index 2b6a8ae..6656489 100644
--- a/src/main/java/com/back/catchmate/domain/board/converter/BoardConverter.java
+++ b/src/main/java/com/back/catchmate/domain/board/converter/BoardConverter.java
@@ -83,10 +83,10 @@ public BoardInfo toBoardInfo(Long boardId) {
                 .liftUpDate(board.getLiftUpDate())
                 .gameInfo(gameInfo)
                 .userInfo(userInfo)
+                .chatRoomId(board.getChatRoom().getId())
                 .build();
     }
 
-
     public BoardInfo toBoardInfo(Board board, Game game) {
         GameInfo gameInfo = gameConverter.toGameInfo(game);
         UserInfo userInfo = userConverter.toUserInfo(board.getUser());
@@ -122,6 +122,7 @@ public BoardInfo toBoardInfo(Board board, Game game, boolean isBookMarked, Strin
                 .buttonStatus(buttonStatus)
                 .gameInfo(gameInfo)
                 .userInfo(userInfo)
+                .chatRoomId(board.getChatRoom().getId())
                 .build();
     }
 
diff --git a/src/main/java/com/back/catchmate/domain/board/dto/BoardResponse.java b/src/main/java/com/back/catchmate/domain/board/dto/BoardResponse.java
index 392deea..9a5c1b7 100644
--- a/src/main/java/com/back/catchmate/domain/board/dto/BoardResponse.java
+++ b/src/main/java/com/back/catchmate/domain/board/dto/BoardResponse.java
@@ -30,6 +30,7 @@ public static class BoardInfo {
         private UserInfo userInfo;
         private boolean isBookMarked;
         private String buttonStatus;
+        private Long chatRoomId;
     }
 
     @Getter
diff --git a/src/main/java/com/back/catchmate/domain/chat/controller/ChatController.java b/src/main/java/com/back/catchmate/domain/chat/controller/ChatController.java
index 60d4659..2e68c5d 100644
--- a/src/main/java/com/back/catchmate/domain/chat/controller/ChatController.java
+++ b/src/main/java/com/back/catchmate/domain/chat/controller/ChatController.java
@@ -18,7 +18,6 @@
 import org.springframework.web.bind.annotation.RequestMapping;
 import org.springframework.web.bind.annotation.RequestParam;
 import org.springframework.web.bind.annotation.RestController;
-import reactor.core.publisher.Mono;
 
 @Tag(name = "채팅 관련 API")
 @RestController
diff --git a/src/main/java/com/back/catchmate/domain/chat/converter/ChatMessageConverter.java b/src/main/java/com/back/catchmate/domain/chat/converter/ChatMessageConverter.java
index cbbafbe..de44553 100644
--- a/src/main/java/com/back/catchmate/domain/chat/converter/ChatMessageConverter.java
+++ b/src/main/java/com/back/catchmate/domain/chat/converter/ChatMessageConverter.java
@@ -1,16 +1,23 @@
 package com.back.catchmate.domain.chat.converter;
 
 import com.back.catchmate.domain.chat.dto.ChatResponse;
+import com.back.catchmate.domain.chat.dto.ChatResponse.ChatMessageInfo;
 import com.back.catchmate.domain.chat.entity.ChatMessage;
 import org.springframework.data.domain.Page;
 import org.springframework.stereotype.Component;
 
+import java.time.LocalDateTime;
+import java.time.ZoneId;
+import java.time.format.DateTimeFormatter;
 import java.util.List;
+import java.util.Locale;
+
+import static com.back.catchmate.domain.chat.dto.ChatRequest.ChatMessageRequest.MessageType;
 
 @Component
 public class ChatMessageConverter {
     public ChatResponse.PagedChatMessageInfo toPagedChatMessageInfo(Page<ChatMessage> chatMessageList) {
-        List<ChatResponse.ChatMessageInfo> chatMessageInfoList = chatMessageList.stream()
+        List<ChatMessageInfo> chatMessageInfoList = chatMessageList.stream()
                 .map(this::toChatMessageInfo)
                 .toList();
 
@@ -23,8 +30,8 @@ public ChatResponse.PagedChatMessageInfo toPagedChatMessageInfo(Page<ChatMessage
                 .build();
     }
 
-    private ChatResponse.ChatMessageInfo toChatMessageInfo(ChatMessage chatMessage) {
-        return ChatResponse.ChatMessageInfo.builder()
+    private ChatMessageInfo toChatMessageInfo(ChatMessage chatMessage) {
+        return ChatMessageInfo.builder()
                 .id(chatMessage.getId())
                 .roomId(chatMessage.getRoomId())
                 .content(chatMessage.getContent())
@@ -32,11 +39,27 @@ private ChatResponse.ChatMessageInfo toChatMessageInfo(ChatMessage chatMessage)
                 .build();
     }
 
-    public ChatMessage toChatMessage(Long chatRoomId, String content, Long senderId) {
+    public ChatMessage toChatMessage(Long chatRoomId, String content, Long senderId, MessageType messageType) {
         return ChatMessage.builder()
                 .roomId(chatRoomId)
                 .content(content)
                 .senderId(senderId)
+                .sendTime(LocalDateTime.now(ZoneId.of("Asia/Seoul")))
+                .messageType(messageType.name())
+                .build();
+    }
+
+    public ChatMessage toDateMessage(Long chatRoomId, LocalDateTime localDateTime) {
+        return ChatMessage.builder()
+                .roomId(chatRoomId)
+                .content(formatDate(localDateTime))
+                .senderId(-1L)
+                .messageType(MessageType.DATE.name())
                 .build();
     }
+
+    private String formatDate(LocalDateTime dateTime) {
+        DateTimeFormatter formatter = DateTimeFormatter.ofPattern("M월 d일", Locale.KOREAN);
+        return dateTime.format(formatter);
+    }
 }
diff --git a/src/main/java/com/back/catchmate/domain/chat/dto/ChatRequest.java b/src/main/java/com/back/catchmate/domain/chat/dto/ChatRequest.java
index 3fd6b03..3e9cbd7 100644
--- a/src/main/java/com/back/catchmate/domain/chat/dto/ChatRequest.java
+++ b/src/main/java/com/back/catchmate/domain/chat/dto/ChatRequest.java
@@ -5,8 +5,6 @@
 import lombok.Getter;
 import lombok.NoArgsConstructor;
 
-import java.time.LocalDateTime;
-
 public abstract class ChatRequest {
     @Getter
     @Builder
@@ -14,12 +12,11 @@ public abstract class ChatRequest {
     @AllArgsConstructor
     public static class ChatMessageRequest {
         public enum MessageType {
-            ENTER, TALK, LEAVE;
+            ENTER, TALK, LEAVE, DATE;
         }
 
         private MessageType messageType;
         private Long senderId;   // 보낸 사람
         private String content;  // 메시지 내용
-        private LocalDateTime sendTime;
     }
 }
diff --git a/src/main/java/com/back/catchmate/domain/chat/entity/ChatMessage.java b/src/main/java/com/back/catchmate/domain/chat/entity/ChatMessage.java
index 964e389..20e9641 100644
--- a/src/main/java/com/back/catchmate/domain/chat/entity/ChatMessage.java
+++ b/src/main/java/com/back/catchmate/domain/chat/entity/ChatMessage.java
@@ -8,6 +8,8 @@
 import org.bson.types.ObjectId;
 import org.springframework.data.mongodb.core.mapping.Document;
 
+import java.time.LocalDateTime;
+
 @Document(collection = "chatting_content") // 실제 몽고 DB 컬렉션 이름
 @Getter
 @Builder
@@ -19,10 +21,6 @@ public class ChatMessage {
     private Long roomId;
     private String content;
     private Long senderId;
-
-    public ChatMessage(Long roomId, String content, Long senderId) {
-        this.roomId = roomId;
-        this.content = content;
-        this.senderId = senderId;
-    }
+    private LocalDateTime sendTime;
+    private String messageType;
 }
diff --git a/src/main/java/com/back/catchmate/domain/chat/repository/ChatMessageRepository.java b/src/main/java/com/back/catchmate/domain/chat/repository/ChatMessageRepository.java
index bced0a1..a67148c 100644
--- a/src/main/java/com/back/catchmate/domain/chat/repository/ChatMessageRepository.java
+++ b/src/main/java/com/back/catchmate/domain/chat/repository/ChatMessageRepository.java
@@ -7,4 +7,6 @@
 
 public interface ChatMessageRepository extends MongoRepository<ChatMessage, String> {
     Page<ChatMessage> findByRoomIdOrderByIdDesc(Long roomId, Pageable pageable);
+
+    ChatMessage findFirstByRoomIdOrderBySendTimeDesc(Long roomId);
 }
diff --git a/src/main/java/com/back/catchmate/domain/chat/service/ChatServiceImpl.java b/src/main/java/com/back/catchmate/domain/chat/service/ChatServiceImpl.java
index 74ab45d..c4a4440 100644
--- a/src/main/java/com/back/catchmate/domain/chat/service/ChatServiceImpl.java
+++ b/src/main/java/com/back/catchmate/domain/chat/service/ChatServiceImpl.java
@@ -4,7 +4,9 @@
 import com.back.catchmate.domain.chat.dto.ChatRequest.ChatMessageRequest;
 import com.back.catchmate.domain.chat.dto.ChatResponse.PagedChatMessageInfo;
 import com.back.catchmate.domain.chat.entity.ChatMessage;
+import com.back.catchmate.domain.chat.entity.ChatRoom;
 import com.back.catchmate.domain.chat.repository.ChatMessageRepository;
+import com.back.catchmate.domain.chat.repository.ChatRoomRepository;
 import com.back.catchmate.domain.chat.repository.UserChatRoomRepository;
 import com.back.catchmate.global.error.ErrorCode;
 import com.back.catchmate.global.error.exception.BaseException;
@@ -16,6 +18,9 @@
 import org.springframework.stereotype.Service;
 import org.springframework.transaction.annotation.Transactional;
 
+import java.time.LocalDate;
+import java.time.LocalDateTime;
+
 import static com.back.catchmate.domain.chat.dto.ChatRequest.ChatMessageRequest.MessageType;
 
 @Slf4j
@@ -24,6 +29,7 @@
 public class ChatServiceImpl implements ChatService {
     private final SimpMessagingTemplate messagingTemplate;
     private final ChatMessageRepository chatMessageRepository;
+    private final ChatRoomRepository chatRoomRepository;
     private final UserChatRoomRepository userChatRoomRepository;
     private final ChatMessageConverter chatMessageConverter;
 
@@ -31,16 +37,43 @@ public class ChatServiceImpl implements ChatService {
     @Override
     @Transactional
     public void sendMessage(Long chatRoomId, ChatMessageRequest request) {
+        String destination = "/topic/chat." + chatRoomId;
+
         if (request.getMessageType() == MessageType.TALK) {
-            ChatMessage chatMessage = chatMessageConverter.toChatMessage(chatRoomId, request.getContent(), request.getSenderId());
+            // 날짜 메시지가 필요한지 확인
+            if (isNewDateMessageNeeded(chatRoomId, LocalDateTime.now())) {
+                ChatMessage dateMessage = chatMessageConverter.toDateMessage(chatRoomId, LocalDateTime.now());
+                messagingTemplate.convertAndSend(destination, dateMessage);
+                chatMessageRepository.insert(dateMessage);
+            }
+
+            ChatMessage chatMessage = chatMessageConverter.toChatMessage(chatRoomId, request.getContent(), request.getSenderId(), MessageType.TALK);
             chatMessageRepository.insert(chatMessage);
+
+            ChatRoom chatRoom = chatRoomRepository.findById(chatRoomId)
+                    .orElseThrow(() -> new BaseException(ErrorCode.CHATROOM_NOT_FOUND));
+
+            chatRoom.updateLastMessageTime();
         }
 
-        String destination = "/topic/chat." + chatRoomId;
         log.info("Sending message to: {}", destination);
         messagingTemplate.convertAndSend(destination, request);
     }
 
+    private boolean isNewDateMessageNeeded(Long chatRoomId, LocalDateTime newMessageTime) {
+        LocalDate newDate = newMessageTime.toLocalDate();
+        ChatMessage chatMessage = chatMessageRepository.findFirstByRoomIdOrderBySendTimeDesc(chatRoomId);
+
+        if (chatMessage == null) {
+            return true;
+        } else {
+            LocalDate localDate = chatMessage.getSendTime().toLocalDate();
+            return !localDate.equals(newDate);
+        }
+    }
+
+    @Override
+    @Transactional(readOnly = true)
     public PagedChatMessageInfo getChatMessageList(Long userId, Long chatRoomId, Pageable pageable) {
         if (!userChatRoomRepository.existsByUserIdAndChatRoomId(userId, chatRoomId)) {
             throw new BaseException(ErrorCode.USER_CHATROOM_NOT_FOUND);