diff --git a/osu.Game.Tests/Database/LegacyExporterTest.cs b/osu.Game.Tests/Database/LegacyExporterTest.cs
index c9aea80585..d41b3a5017 100644
--- a/osu.Game.Tests/Database/LegacyExporterTest.cs
+++ b/osu.Game.Tests/Database/LegacyExporterTest.cs
@@ -46,7 +46,7 @@ namespace osu.Game.Tests.Database
             Assert.That(item.Filename.Length, Is.LessThan(TestLegacyExporter.MAX_FILENAME_LENGTH));
 
             //Export multiple times
-            for (int i = 0; i < 10; i++)
+            for (int i = 0; i < 100; i++)
             {
                 string expectedFileName = i == 0 ? short_filename : $"{short_filename} ({i})";
                 exportItemAndAssert(item, expectedFileName);
@@ -76,8 +76,11 @@ namespace osu.Game.Tests.Database
             Assert.That(item.Filename.Length, Is.GreaterThan(TestLegacyExporter.MAX_FILENAME_LENGTH));
 
             //Export multiple times
-            for (int i = 0; i < 10; i++)
-                exportItemAndAssert(item, expectedName);
+            for (int i = 0; i < 100; i++)
+            {
+                string expectedFilename = i == 0 ? expectedName : $"{expectedName} ({i})";
+                exportItemAndAssert(item, expectedFilename);
+            }
         }
 
         private void exportItemAndAssert(IHasNamedFiles item, string expectedName)
diff --git a/osu.Game/Database/LegacyExporter.cs b/osu.Game/Database/LegacyExporter.cs
index cf88efb151..0fa7b9e03c 100644
--- a/osu.Game/Database/LegacyExporter.cs
+++ b/osu.Game/Database/LegacyExporter.cs
@@ -31,7 +31,7 @@ namespace osu.Game.Database
         /// For more information see <see href="https://www.ibm.com/docs/en/spectrum-protect/8.1.9?topic=parameters-file-specification-syntax">file specification syntax</see>, <seealso href="https://en.wikipedia.org/wiki/Comparison_of_file_systems#Limits">file systems limitations</seealso>
         /// </para>
         /// </remarks>
-        public const int MAX_FILENAME_LENGTH = 255 - (32 + 4 + 2); //max path - (Guid + Guid "D" format chars + Storage.CreateFileSafely chars)
+        public const int MAX_FILENAME_LENGTH = 255 - (32 + 4 + 2 + 5); //max path - (Guid + Guid "D" format chars + Storage.CreateFileSafely chars + account for ' (99)' suffix)
 
         /// <summary>
         /// The file extension for exports (including the leading '.').
@@ -48,7 +48,15 @@ namespace osu.Game.Database
             UserFileStorage = storage.GetStorageForDirectory(@"files");
         }
 
-        protected virtual string GetFilename(TModel item) => item.GetDisplayString();
+        protected virtual string GetFilename(TModel item)
+        {
+            string filename = item.GetDisplayString();
+
+            if (filename.Length > MAX_FILENAME_LENGTH - FileExtension.Length)
+                return filename.Remove(MAX_FILENAME_LENGTH - FileExtension.Length);
+
+            return filename;
+        }
 
         /// <summary>
         /// Exports an item to a legacy (.zip based) package.
@@ -65,14 +73,6 @@ namespace osu.Game.Database
 
             string filename = NamingUtils.GetNextBestFilename(existingExports, $"{itemFilename}{FileExtension}");
 
-            if (filename.Length > MAX_FILENAME_LENGTH)
-            {
-                string filenameWithoutExtension = Path.GetFileNameWithoutExtension(filename);
-
-                filenameWithoutExtension = filenameWithoutExtension.Remove(MAX_FILENAME_LENGTH - FileExtension.Length);
-                filename = $"{filenameWithoutExtension}{FileExtension}";
-            }
-
             using (var stream = exportStorage.CreateFileSafely(filename))
                 ExportModelTo(item, stream);