diff --git a/python/packages/autogen-core/src/autogen_core/model_context/_token_limited_chat_completion_context.py b/python/packages/autogen-core/src/autogen_core/model_context/_token_limited_chat_completion_context.py
index b8a0258a4d62..6336458f5241 100644
--- a/python/packages/autogen-core/src/autogen_core/model_context/_token_limited_chat_completion_context.py
+++ b/python/packages/autogen-core/src/autogen_core/model_context/_token_limited_chat_completion_context.py
@@ -4,7 +4,7 @@
 from typing_extensions import Self
 
 from .._component_config import Component, ComponentModel
-from ..models import ChatCompletionClient, FunctionExecutionResultMessage, LLMMessage
+from ..models import AssistantMessage, ChatCompletionClient, FunctionExecutionResultMessage, LLMMessage
 from ..tools import ToolSchema
 from ._chat_completion_context import ChatCompletionContext
 
@@ -16,6 +16,27 @@ class TokenLimitedChatCompletionContextConfig(BaseModel):
     initial_messages: List[LLMMessage] | None = None
 
 
+def _is_function_call_message(message: LLMMessage) -> bool:
+    return isinstance(message, AssistantMessage) and isinstance(message.content, list)
+
+
+def _remove_middle_message(messages: List[LLMMessage]) -> None:
+    """Remove the middle message without splitting an adjacent tool call/result pair."""
+    middle_index = len(messages) // 2
+    message = messages[middle_index]
+
+    if _is_function_call_message(message):
+        if middle_index + 1 < len(messages) and isinstance(messages[middle_index + 1], FunctionExecutionResultMessage):
+            del messages[middle_index : middle_index + 2]
+            return
+    elif isinstance(message, FunctionExecutionResultMessage):
+        if middle_index > 0 and _is_function_call_message(messages[middle_index - 1]):
+            del messages[middle_index - 1 : middle_index + 1]
+            return
+
+    messages.pop(middle_index)
+
+
 class TokenLimitedChatCompletionContext(ChatCompletionContext, Component[TokenLimitedChatCompletionContextConfig]):
     """(Experimental) A token based chat completion context maintains a view of the context up to a token limit.
 
@@ -61,14 +82,12 @@ async def get_messages(self) -> List[LLMMessage]:
         if self._token_limit is None:
             remaining_tokens = self._model_client.remaining_tokens(messages, tools=self._tool_schema)
             while remaining_tokens < 0 and len(messages) > 0:
-                middle_index = len(messages) // 2
-                messages.pop(middle_index)
+                _remove_middle_message(messages)
                 remaining_tokens = self._model_client.remaining_tokens(messages, tools=self._tool_schema)
         else:
             token_count = self._model_client.count_tokens(messages, tools=self._tool_schema)
             while token_count > self._token_limit and len(messages) > 0:
-                middle_index = len(messages) // 2
-                messages.pop(middle_index)
+                _remove_middle_message(messages)
                 token_count = self._model_client.count_tokens(messages, tools=self._tool_schema)
         if messages and isinstance(messages[0], FunctionExecutionResultMessage):
             # Handle the first message is a function call result message.
diff --git a/python/packages/autogen-core/tests/test_model_context.py b/python/packages/autogen-core/tests/test_model_context.py
index bcd2a9c87d9e..9d9c678f865e 100644
--- a/python/packages/autogen-core/tests/test_model_context.py
+++ b/python/packages/autogen-core/tests/test_model_context.py
@@ -1,6 +1,8 @@
-from typing import List
+from typing import List, Sequence
+from unittest.mock import MagicMock
 
 import pytest
+from autogen_core import FunctionCall
 from autogen_core.model_context import (
     BufferedChatCompletionContext,
     HeadAndTailChatCompletionContext,
@@ -10,6 +12,7 @@
 from autogen_core.models import (
     AssistantMessage,
     ChatCompletionClient,
+    FunctionExecutionResult,
     FunctionExecutionResultMessage,
     LLMMessage,
     UserMessage,
@@ -208,3 +211,44 @@ async def test_token_limited_model_context_openai_with_function_result(
     assert type(retrieved[0]) == UserMessage  # Function result should be removed
     assert type(retrieved[1]) == AssistantMessage
     assert type(retrieved[2]) == UserMessage
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("pair_start", [2, 3], ids=["result-at-middle", "call-at-middle"])
+@pytest.mark.parametrize("token_limit", [6, None], ids=["count-tokens", "remaining-tokens"])
+async def test_token_limited_model_context_keeps_function_call_result_pairs(
+    pair_start: int, token_limit: int | None
+) -> None:
+    def count_tokens(messages: Sequence[LLMMessage], **_: object) -> int:
+        return len(messages)
+
+    def remaining_tokens(messages: Sequence[LLMMessage], **_: object) -> int:
+        return 6 - len(messages)
+
+    model_client = MagicMock(spec=ChatCompletionClient)
+    model_client.count_tokens.side_effect = count_tokens
+    model_client.remaining_tokens.side_effect = remaining_tokens
+    model_context = TokenLimitedChatCompletionContext(model_client=model_client, token_limit=token_limit)
+
+    function_call = AssistantMessage(
+        content=[FunctionCall(id="call_1", arguments="{}", name="tool")], source="assistant"
+    )
+    function_result = FunctionExecutionResultMessage(
+        content=[FunctionExecutionResult(content="ok", name="tool", call_id="call_1")]
+    )
+    messages: List[LLMMessage] = [
+        UserMessage(content="m0", source="user"),
+        UserMessage(content="m1", source="user"),
+        UserMessage(content="m2", source="user"),
+        UserMessage(content="m3", source="user"),
+        UserMessage(content="m4", source="user"),
+    ]
+    messages[pair_start:pair_start] = [function_call, function_result]
+    for message in messages:
+        await model_context.add_message(message)
+
+    retrieved = await model_context.get_messages()
+
+    assert function_call not in retrieved
+    assert function_result not in retrieved
+    assert len(retrieved) == 5