diff --git a/src/libraries/Microsoft.Extensions.FileSystemGlobbing/src/InMemoryDirectoryInfo.cs b/src/libraries/Microsoft.Extensions.FileSystemGlobbing/src/InMemoryDirectoryInfo.cs
index 8d6c9c3f33e4aa..51ed8ec44e2f54 100644
--- a/src/libraries/Microsoft.Extensions.FileSystemGlobbing/src/InMemoryDirectoryInfo.cs
+++ b/src/libraries/Microsoft.Extensions.FileSystemGlobbing/src/InMemoryDirectoryInfo.cs
@@ -17,24 +17,38 @@ public class InMemoryDirectoryInfo : DirectoryInfoBase
     {
         private static readonly char[] DirectorySeparators = new[] { Path.DirectorySeparatorChar, Path.AltDirectorySeparatorChar };
         private readonly IEnumerable<string> _files;
+        private readonly StringComparison _comparisonType;
 
         /// <summary>
-        /// Creates a new InMemoryDirectoryInfo with the root directory and files given.
+        /// Creates a new case-sensitive InMemoryDirectoryInfo with the root directory and files given.
         /// </summary>
         /// <param name="rootDir">The root directory that this FileSystem will use.</param>
         /// <param name="files">Collection of file names. If relative paths <paramref name="rootDir"/> will be prepended to the paths.</param>
         public InMemoryDirectoryInfo(string rootDir, IEnumerable<string>? files)
-            : this(rootDir, files, false)
+            : this(rootDir, files, false, StringComparison.Ordinal)
+        {
+        }
+
+        /// <summary>
+        /// Creates a new InMemoryDirectoryInfo with the root directory and files given.
+        /// </summary>
+        /// <param name="rootDir">The root directory that this FileSystem will use.</param>
+        /// <param name="files">Collection of file names. If relative paths <paramref name="rootDir"/> will be prepended to the paths.</param>
+        /// <param name="comparisonType">The comparison type for the root directory. When files are enumerated they will be compared with the root directory using this comparison type.</param>
+        internal InMemoryDirectoryInfo(string rootDir, IEnumerable<string>? files, StringComparison comparisonType)
+            : this(rootDir, files, false, comparisonType)
         {
         }
 
-        private InMemoryDirectoryInfo(string rootDir, IEnumerable<string>? files, bool normalized)
+        private InMemoryDirectoryInfo(string rootDir, IEnumerable<string>? files, bool normalized, StringComparison comparisonType)
         {
             if (string.IsNullOrEmpty(rootDir))
             {
                 throw new ArgumentNullException(nameof(rootDir));
             }
 
+            _comparisonType = comparisonType;
+
             files ??= new List<string>();
 
             Name = Path.GetFileName(rootDir);
@@ -76,7 +90,7 @@ private InMemoryDirectoryInfo(string rootDir, IEnumerable<string>? files, bool n
 
         /// <inheritdoc />
         public override DirectoryInfoBase? ParentDirectory =>
-            new InMemoryDirectoryInfo(Path.GetDirectoryName(FullName)!, _files, true);
+            new InMemoryDirectoryInfo(Path.GetDirectoryName(FullName)!, _files, true, _comparisonType);
 
         /// <inheritdoc />
         public override IEnumerable<FileSystemInfoBase> EnumerateFileSystemInfos()
@@ -113,15 +127,15 @@ public override IEnumerable<FileSystemInfoBase> EnumerateFileSystemInfos()
 
             foreach (KeyValuePair<string, List<string>> item in dict)
             {
-                yield return new InMemoryDirectoryInfo(item.Key, item.Value, true);
+                yield return new InMemoryDirectoryInfo(item.Key, item.Value, true, _comparisonType);
             }
         }
 
-        private static bool IsRootDirectory(string rootDir, string filePath)
+        private bool IsRootDirectory(string rootDir, string filePath)
         {
             int rootDirLength = rootDir.Length;
 
-            return filePath.StartsWith(rootDir, StringComparison.Ordinal) &&
+            return filePath.StartsWith(rootDir, _comparisonType) &&
                 (rootDir[rootDirLength - 1] == Path.DirectorySeparatorChar ||
                 filePath.IndexOf(Path.DirectorySeparatorChar, rootDirLength) == rootDirLength);
         }
@@ -131,12 +145,12 @@ public override DirectoryInfoBase GetDirectory(string path)
         {
             if (string.Equals(path, "..", StringComparison.Ordinal))
             {
-                return new InMemoryDirectoryInfo(Path.Combine(FullName, path), _files, true);
+                return new InMemoryDirectoryInfo(Path.Combine(FullName, path), _files, true, _comparisonType);
             }
             else
             {
                 string normPath = Path.GetFullPath(path.Replace(Path.AltDirectorySeparatorChar, Path.DirectorySeparatorChar));
-                return new InMemoryDirectoryInfo(normPath, _files, true);
+                return new InMemoryDirectoryInfo(normPath, _files, true, _comparisonType);
             }
         }
 
diff --git a/src/libraries/Microsoft.Extensions.FileSystemGlobbing/src/Matcher.cs b/src/libraries/Microsoft.Extensions.FileSystemGlobbing/src/Matcher.cs
index 61503f7e0e4761..b3bf45b5af1736 100644
--- a/src/libraries/Microsoft.Extensions.FileSystemGlobbing/src/Matcher.cs
+++ b/src/libraries/Microsoft.Extensions.FileSystemGlobbing/src/Matcher.cs
@@ -100,9 +100,10 @@ public class Matcher
         private readonly List<IPattern>? _excludePatterns;
         private readonly List<IncludeOrExcludeValue<IPattern>>? _includeOrExcludePatterns;
         private readonly PatternBuilder _builder;
-        private readonly StringComparison _comparison;
         private readonly bool _preserveFilterOrder;
 
+        internal StringComparison ComparisonType { get; }
+
         /// <summary>
         /// Initializes an instance of <see cref="Matcher" /> using case-insensitive matching
         /// </summary>
@@ -130,7 +131,7 @@ public Matcher(StringComparison comparisonType)
         /// </param>
         public Matcher(StringComparison comparisonType = StringComparison.OrdinalIgnoreCase, bool preserveFilterOrder = false)
         {
-            _comparison = comparisonType;
+            ComparisonType = comparisonType;
             _builder = new PatternBuilder(comparisonType);
             _preserveFilterOrder = preserveFilterOrder;
 
@@ -199,8 +200,8 @@ public virtual PatternMatchingResult Execute(DirectoryInfoBase directoryInfo)
             ArgumentNullException.ThrowIfNull(directoryInfo);
 
             return _preserveFilterOrder ?
-                new MatcherContext(_includeOrExcludePatterns!, directoryInfo, _comparison).Execute() :
-                new MatcherContext(_includePatterns!, _excludePatterns!, directoryInfo, _comparison).Execute();
+                new MatcherContext(_includeOrExcludePatterns!, directoryInfo, ComparisonType).Execute() :
+                new MatcherContext(_includePatterns!, _excludePatterns!, directoryInfo, ComparisonType).Execute();
         }
     }
 }
diff --git a/src/libraries/Microsoft.Extensions.FileSystemGlobbing/src/MatcherExtensions.cs b/src/libraries/Microsoft.Extensions.FileSystemGlobbing/src/MatcherExtensions.cs
index b18877202c2c37..8c26745aa28efd 100644
--- a/src/libraries/Microsoft.Extensions.FileSystemGlobbing/src/MatcherExtensions.cs
+++ b/src/libraries/Microsoft.Extensions.FileSystemGlobbing/src/MatcherExtensions.cs
@@ -111,7 +111,7 @@ public static PatternMatchingResult Match(this Matcher matcher, string rootDir,
         {
             ArgumentNullException.ThrowIfNull(matcher);
 
-            return matcher.Execute(new InMemoryDirectoryInfo(rootDir, files));
+            return matcher.Execute(new InMemoryDirectoryInfo(rootDir, files, matcher.ComparisonType));
         }
     }
 }
diff --git a/src/libraries/Microsoft.Extensions.FileSystemGlobbing/tests/FunctionalTests.cs b/src/libraries/Microsoft.Extensions.FileSystemGlobbing/tests/FunctionalTests.cs
index e8bcdacdb9558b..63e06e841184af 100644
--- a/src/libraries/Microsoft.Extensions.FileSystemGlobbing/tests/FunctionalTests.cs
+++ b/src/libraries/Microsoft.Extensions.FileSystemGlobbing/tests/FunctionalTests.cs
@@ -901,5 +901,50 @@ public void VerifyFiles_ParentRedundantSegment_CurrentDirectory_HasMatches()
                 Assert.True(matcher.Match([$"../{cwdFolderName}/{file}"]).HasMatches);
             }
         }
+
+        [Theory]
+        [InlineData(@"/this/example/root", @"/this/EXAMPLE/root", "**/*", new[] { "some/test/file.txt" })]
+        [InlineData(@"/this/example/root", @"/this/example/root", "**/*", new[] { "some/test/file.txt" })]
+        [InlineData(@"/this/EXAMPLE/root", @"/this/example/root", "**/*", new[] { "some/test/file.txt" })]
+        public void VerifyFiles_InMemory_HasCaseInsensitiveRootMatches(string matchRoot, string filesRoot, string pattern, string[] expectedSubPaths)
+        {
+            Matcher matcher = new(StringComparison.OrdinalIgnoreCase);
+            matcher.AddInclude(pattern);
+
+            PatternMatchingResult patternMatchingResult = matcher.Match(matchRoot,
+                expectedSubPaths.Select(expectedSubPath => Path.Combine(filesRoot, expectedSubPath)));
+
+            Assert.True(patternMatchingResult.HasMatches);
+            Assert.Equal(expectedSubPaths.Length, patternMatchingResult.Files.Count());
+        }
+
+        [Theory]
+        [InlineData(@"/this/example/root", @"/this/example/root", "**/*", new[] { "some/test/file.txt" })]
+        public void VerifyFiles_InMemory_HasCaseSensitiveRootMatches(string matchRoot, string filesRoot, string pattern, string[] expectedSubPaths)
+        {
+            Matcher matcher = new(StringComparison.Ordinal);
+            matcher.AddInclude(pattern);
+
+            PatternMatchingResult patternMatchingResult = matcher.Match(matchRoot,
+                expectedSubPaths.Select(expectedSubPath => Path.Combine(filesRoot, expectedSubPath)));
+
+            Assert.True(patternMatchingResult.HasMatches);
+            Assert.Equal(expectedSubPaths.Length, patternMatchingResult.Files.Count());
+        }
+
+        [Theory]
+        [InlineData(@"/this/example/root", @"/this/EXAMPLE/root", "**/*", new[] { "some/test/file.txt" })]
+        [InlineData(@"/this/EXAMPLE/root", @"/this/example/root", "**/*", new[] { "some/test/file.txt" })]
+        public void VerifyFiles_InMemory_HasCaseSensitiveRootMisses(string matchRoot, string filesRoot, string pattern, string[] expectedSubPaths)
+        {
+            Matcher matcher = new(StringComparison.Ordinal);
+            matcher.AddInclude(pattern);
+
+            PatternMatchingResult patternMatchingResult = matcher.Match(matchRoot,
+                expectedSubPaths.Select(expectedSubPath => Path.Combine(filesRoot, expectedSubPath)));
+
+            Assert.False(patternMatchingResult.HasMatches);
+            Assert.Equal(0, patternMatchingResult.Files.Count());
+        }
     }
 }