diff --git a/tools/code-owners-parser/Azure.Sdk.Tools.CodeOwnersParser.Tests/CodeownersFileTests.cs b/tools/code-owners-parser/Azure.Sdk.Tools.CodeOwnersParser.Tests/CodeownersFileTests.cs
index ab96bca6284..acc3ca06d43 100644
--- a/tools/code-owners-parser/Azure.Sdk.Tools.CodeOwnersParser.Tests/CodeownersFileTests.cs
+++ b/tools/code-owners-parser/Azure.Sdk.Tools.CodeOwnersParser.Tests/CodeownersFileTests.cs
@@ -94,6 +94,12 @@ public class CodeownersFileTests
         new(       "/**" , "["           ,  false , false ),
         new(       "/**" , "]"           ,  false , false ),
         new(       "/**" , "!"           ,  false , false ),
+        new(       "/a*" , "a"           ,  false , true  ),
+        new(       "/a*" , "a/x"         ,  false , true  ),
+        new(       "/a*" , "a/x/d"       ,  false , true  ),
+        new(       "/a*" , "ab"          ,  false , true  ),
+        new(       "/a*" , "ab/x"        ,  false , true  ),
+        new(       "/a*" , "ab/x/d"      ,  false , true  ),
         new(     "/a/**" , "a"           ,  false , false ),
         new(     "/*/**" , "a"           ,  false , false ),
         new(     "/*/**" , "a/"          ,  false , false ),
diff --git a/tools/code-owners-parser/CodeOwnersParser/MatchedCodeownersEntry.cs b/tools/code-owners-parser/CodeOwnersParser/MatchedCodeownersEntry.cs
index 56db516e998..77ebf40b6e5 100644
--- a/tools/code-owners-parser/CodeOwnersParser/MatchedCodeownersEntry.cs
+++ b/tools/code-owners-parser/CodeOwnersParser/MatchedCodeownersEntry.cs
@@ -227,9 +227,16 @@ private static string SetPatternSuffix(string pattern)
             // even though in such case the path might be a path to a directory.
             if (!pattern.EndsWith("/"))
             {
-                // Append "end of string" symbol, denoting the match has to be exact,
-                // not a substring, as we are dealing with a file.
-                pattern += "$";
+                // Manual experiments with how GitHub applies ownership show
+                // that a path like "/foo*" is effectively equivalent to 
+                // "Match any path with prefix of '/foo'".
+                // Hence, we are not appending "$" if this is the case.
+                if (!pattern.EndsWith(SingleStar))
+                {
+                    // Append "end of string" symbol, denoting the match has to be exact,
+                    // not a substring, as we are dealing with a file.
+                    pattern += "$";
+                }
             }
             else // The pattern ends with "/", denoting it is a directory.
             {