diff --git a/osu.Game.Tests/Visual/Online/TestSceneStandAloneChatDisplay.cs b/osu.Game.Tests/Visual/Online/TestSceneStandAloneChatDisplay.cs
index 7d2ac90939..ebd5e12acb 100644
--- a/osu.Game.Tests/Visual/Online/TestSceneStandAloneChatDisplay.cs
+++ b/osu.Game.Tests/Visual/Online/TestSceneStandAloneChatDisplay.cs
@@ -73,6 +73,11 @@ public void SetUp() => Schedule(() =>
             messageIdSequence = 0;
             channelManager.CurrentChannel.Value = testChannel = new Channel();
 
+            reinitialiseDrawableDisplay();
+        });
+
+        private void reinitialiseDrawableDisplay()
+        {
             Children = new[]
             {
                 chatDisplay = new TestStandAloneChatDisplay
@@ -92,13 +97,14 @@ public void SetUp() => Schedule(() =>
                     Channel = { Value = testChannel },
                 }
             };
-        });
+        }
 
         [Test]
         public void TestSystemMessageOrdering()
         {
             var standardMessage = new Message(messageIdSequence++)
             {
+                Timestamp = DateTimeOffset.Now,
                 Sender = admin,
                 Content = "I am a wang!"
             };
@@ -106,14 +112,45 @@ public void TestSystemMessageOrdering()
             var infoMessage1 = new InfoMessage($"the system is calling {messageIdSequence++}");
             var infoMessage2 = new InfoMessage($"the system is calling {messageIdSequence++}");
 
+            var standardMessage2 = new Message(messageIdSequence++)
+            {
+                Timestamp = DateTimeOffset.Now,
+                Sender = admin,
+                Content = "I am a wang!"
+            };
+
             AddStep("message from admin", () => testChannel.AddNewMessages(standardMessage));
             AddStep("message from system", () => testChannel.AddNewMessages(infoMessage1));
             AddStep("message from system", () => testChannel.AddNewMessages(infoMessage2));
+            AddStep("message from admin", () => testChannel.AddNewMessages(standardMessage2));
 
-            AddAssert("message order is correct", () => testChannel.Messages.Count == 3
-                                                        && testChannel.Messages[0] == standardMessage
-                                                        && testChannel.Messages[1] == infoMessage1
-                                                        && testChannel.Messages[2] == infoMessage2);
+            AddAssert("count is correct", () => testChannel.Messages.Count, () => Is.EqualTo(4));
+
+            AddAssert("message order is correct", () => testChannel.Messages, () => Is.EqualTo(new[]
+            {
+                standardMessage,
+                infoMessage1,
+                infoMessage2,
+                standardMessage2
+            }));
+
+            AddAssert("displayed order is correct", () => chatDisplay.DrawableChannel.ChildrenOfType<ChatLine>().Select(c => c.Message), () => Is.EqualTo(new[]
+            {
+                standardMessage,
+                infoMessage1,
+                infoMessage2,
+                standardMessage2
+            }));
+
+            AddStep("reinit drawable channel", reinitialiseDrawableDisplay);
+
+            AddAssert("displayed order is still correct", () => chatDisplay.DrawableChannel.ChildrenOfType<ChatLine>().Select(c => c.Message), () => Is.EqualTo(new[]
+            {
+                standardMessage,
+                infoMessage1,
+                infoMessage2,
+                standardMessage2
+            }));
         }
 
         [Test]
diff --git a/osu.Game/Online/Chat/InfoMessage.cs b/osu.Game/Online/Chat/InfoMessage.cs
index d98c67de34..2ade99dcb2 100644
--- a/osu.Game/Online/Chat/InfoMessage.cs
+++ b/osu.Game/Online/Chat/InfoMessage.cs
@@ -1,9 +1,6 @@
 // Copyright (c) ppy Pty Ltd <contact@ppy.sh>. Licensed under the MIT Licence.
 // See the LICENCE file in the repository root for full licence text.
 
-#nullable disable
-
-using System;
 using osu.Game.Online.API.Requests.Responses;
 
 namespace osu.Game.Online.Chat
@@ -13,7 +10,6 @@ public class InfoMessage : LocalMessage
         public InfoMessage(string message)
             : base(null)
         {
-            Timestamp = DateTimeOffset.Now;
             Content = message;
 
             Sender = APIUser.SYSTEM_USER;
diff --git a/osu.Game/Online/Chat/LocalEchoMessage.cs b/osu.Game/Online/Chat/LocalEchoMessage.cs
index b226fe6cad..8a39515575 100644
--- a/osu.Game/Online/Chat/LocalEchoMessage.cs
+++ b/osu.Game/Online/Chat/LocalEchoMessage.cs
@@ -1,8 +1,6 @@
 // Copyright (c) ppy Pty Ltd <contact@ppy.sh>. Licensed under the MIT Licence.
 // See the LICENCE file in the repository root for full licence text.
 
-#nullable disable
-
 namespace osu.Game.Online.Chat
 {
     public class LocalEchoMessage : LocalMessage
diff --git a/osu.Game/Online/Chat/LocalMessage.cs b/osu.Game/Online/Chat/LocalMessage.cs
index 5736f5cabf..57caca2287 100644
--- a/osu.Game/Online/Chat/LocalMessage.cs
+++ b/osu.Game/Online/Chat/LocalMessage.cs
@@ -1,7 +1,7 @@
 // Copyright (c) ppy Pty Ltd <contact@ppy.sh>. Licensed under the MIT Licence.
 // See the LICENCE file in the repository root for full licence text.
 
-#nullable disable
+using System;
 
 namespace osu.Game.Online.Chat
 {
@@ -13,6 +13,7 @@ public class LocalMessage : Message
         protected LocalMessage(long? id)
             : base(id)
         {
+            Timestamp = DateTimeOffset.Now;
         }
     }
 }
diff --git a/osu.Game/Online/Chat/Message.cs b/osu.Game/Online/Chat/Message.cs
index 9f6f9c8d6b..8ea3ca0fc7 100644
--- a/osu.Game/Online/Chat/Message.cs
+++ b/osu.Game/Online/Chat/Message.cs
@@ -5,6 +5,7 @@
 
 using System;
 using System.Collections.Generic;
+using System.Threading;
 using Newtonsoft.Json;
 using osu.Game.Online.API.Requests.Responses;
 
@@ -59,19 +60,28 @@ public Message()
         /// <remarks>The <see cref="Link"/>s' <see cref="Link.Index"/> and <see cref="Link.Length"/>s are according to <see cref="DisplayContent"/></remarks>
         public List<Link> Links;
 
+        private static long constructionOrderStatic;
+        private readonly long constructionOrder;
+
         public Message(long? id)
         {
             Id = id;
+
+            constructionOrder = Interlocked.Increment(ref constructionOrderStatic);
         }
 
         public int CompareTo(Message other)
         {
-            if (!Id.HasValue)
-                return other.Id.HasValue ? 1 : Timestamp.CompareTo(other.Timestamp);
-            if (!other.Id.HasValue)
-                return -1;
+            if (Id.HasValue && other.Id.HasValue)
+                return Id.Value.CompareTo(other.Id.Value);
 
-            return Id.Value.CompareTo(other.Id.Value);
+            int timestampComparison = Timestamp.CompareTo(other.Timestamp);
+
+            if (timestampComparison != 0)
+                return timestampComparison;
+
+            // Timestamp might not be accurate enough to make a stable sorting decision.
+            return constructionOrder.CompareTo(other.constructionOrder);
         }
 
         public virtual bool Equals(Message other)
@@ -85,6 +95,6 @@ public virtual bool Equals(Message other)
         // ReSharper disable once ImpureMethodCallOnReadonlyValueField
         public override int GetHashCode() => Id.GetHashCode();
 
-        public override string ToString() => $"[{ChannelId}] ({Id}) {Sender}: {Content}";
+        public override string ToString() => $"({(Id?.ToString() ?? "null")}) {Timestamp} {Sender}: {Content}";
     }
 }