diff --git a/src/System.Management.Automation/engine/debugger/debugger.cs b/src/System.Management.Automation/engine/debugger/debugger.cs
index c91092772bc..68b6d1a296e 100644
--- a/src/System.Management.Automation/engine/debugger/debugger.cs
+++ b/src/System.Management.Automation/engine/debugger/debugger.cs
@@ -982,7 +982,7 @@ internal ScriptDebugger(ExecutionContext context)
             _inBreakpoint = false;
             _idToBreakpoint = new ConcurrentDictionary<int, Breakpoint>();
             // The string key is function context file path. The int key is sequencePoint index.
-            _pendingBreakpoints = new ConcurrentDictionary<string, ConcurrentDictionary<int, LineBreakpoint>>();
+            _pendingBreakpoints = new ConcurrentDictionary<string, ConcurrentDictionary<int, LineBreakpoint>>(StringComparer.OrdinalIgnoreCase);
             _boundBreakpoints = new ConcurrentDictionary<string, Tuple<WeakReference, ConcurrentDictionary<int, LineBreakpoint>>>(StringComparer.OrdinalIgnoreCase);
             _commandBreakpoints = new ConcurrentDictionary<int, CommandBreakpoint>();
             _variableBreakpoints = new ConcurrentDictionary<string, ConcurrentDictionary<int, VariableBreakpoint>>(StringComparer.OrdinalIgnoreCase);
diff --git a/test/powershell/Language/Scripting/Debugging/DebuggerScriptTests.Tests.ps1 b/test/powershell/Language/Scripting/Debugging/DebuggerScriptTests.Tests.ps1
index 1cf588427cc..3dc799f169c 100644
--- a/test/powershell/Language/Scripting/Debugging/DebuggerScriptTests.Tests.ps1
+++ b/test/powershell/Language/Scripting/Debugging/DebuggerScriptTests.Tests.ps1
@@ -643,3 +643,20 @@ Describe "Sometimes line breakpoints are ignored" -Tags "CI" {
         if (Test-Path -Path $tempFileName2) { Remove-Item $tempFileName2 -Force }
     }
 }
+
+Describe 'Breakpoints use case-insensitive match for script paths' -Tags 'CI' {
+    # https://github.com/PowerShell/PowerShell/issues/20044
+    # Running on Windows only as Set-PSBreakpoint does case sensitive check on provided path on Unix
+    It 'Hits breakpoint' -Skip:(!$IsWindows) {
+        $filePath = Join-Path -Path $TestDrive -ChildPath 'demoIssue20044.ps1'
+        Set-Content -Path $filePath -Value "'Hello World'"
+
+        $bp = Set-PSBreakpoint -Script $filePath.ToUpper() -Line 1 -Action { continue }
+
+        & $filePath
+
+        $bp.HitCount | Should -Be 1
+
+        if ($null -ne $bp) { Remove-PSBreakpoint $bp }
+    }
+}