diff --git a/src/libraries/System.Text.RegularExpressions/gen/RegexGenerator.Emitter.cs b/src/libraries/System.Text.RegularExpressions/gen/RegexGenerator.Emitter.cs
index eb2ed60e3e8b0..32e79eef2745e 100644
--- a/src/libraries/System.Text.RegularExpressions/gen/RegexGenerator.Emitter.cs
+++ b/src/libraries/System.Text.RegularExpressions/gen/RegexGenerator.Emitter.cs
@@ -4135,8 +4135,10 @@ void EmitLoop(RegexNode node)
                         writer.WriteLine();
 
                         // Store the loop's state
-                        EmitStackPush(iterationMayBeEmpty ?
-                            new[] { startingPos!, iterationCount } :
+                        EmitStackPush(
+                            startingPos is not null && startingStackpos is not null ? new[] { startingPos, startingStackpos, iterationCount } :
+                            startingPos is not null ? new[] { startingPos, iterationCount } :
+                            startingStackpos is not null ? new[] { startingStackpos, iterationCount } :
                             new[] { iterationCount });
 
                         // Skip past the backtracking section
@@ -4147,8 +4149,10 @@ void EmitLoop(RegexNode node)
                         // Emit a backtracking section that restores the loop's state and then jumps to the previous done label
                         string backtrack = ReserveName("LoopBacktrack");
                         MarkLabel(backtrack, emitSemicolon: false);
-                        EmitStackPop(iterationMayBeEmpty ?
-                            new[] { iterationCount, startingPos! } :
+                        EmitStackPop(
+                            startingPos is not null && startingStackpos is not null ? new[] { iterationCount, startingStackpos, startingPos } :
+                            startingPos is not null ? new[] { iterationCount, startingPos } :
+                            startingStackpos is not null ? new[] { iterationCount, startingStackpos } :
                             new[] { iterationCount });
 
                         // We're backtracking.  Check the timeout.
diff --git a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexCompiler.cs b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexCompiler.cs
index 1c592b9c89fb0..0b363278a5d0b 100644
--- a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexCompiler.cs
+++ b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexCompiler.cs
@@ -4848,11 +4848,15 @@ void EmitLoop(RegexNode node)
                     if (analysis.IsInLoop(node))
                     {
                         // Store the loop's state
-                        EmitStackResizeIfNeeded(1 + (startingPos is not null ? 1 : 0));
+                        EmitStackResizeIfNeeded(1 + (startingPos is not null ? 1 : 0) + (startingStackpos is not null ? 1 : 0));
                         if (startingPos is not null)
                         {
                             EmitStackPush(() => Ldloc(startingPos));
                         }
+                        if (startingStackpos is not null)
+                        {
+                            EmitStackPush(() => Ldloc(startingStackpos));
+                        }
                         EmitStackPush(() => Ldloc(iterationCount));
 
                         // Skip past the backtracking section
@@ -4868,9 +4872,15 @@ void EmitLoop(RegexNode node)
                         EmitTimeoutCheckIfNeeded();
 
                         // iterationCount = base.runstack[--runstack];
+                        // startingStackpos = base.runstack[--runstack];
                         // startingPos = base.runstack[--runstack];
                         EmitStackPop();
                         Stloc(iterationCount);
+                        if (startingStackpos is not null)
+                        {
+                            EmitStackPop();
+                            Stloc(startingStackpos);
+                        }
                         if (startingPos is not null)
                         {
                             EmitStackPop();
diff --git a/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.Match.Tests.cs b/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.Match.Tests.cs
index f138d610e2b94..b75a249d6b555 100644
--- a/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.Match.Tests.cs
+++ b/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.Match.Tests.cs
@@ -392,6 +392,10 @@ public static IEnumerable<object[]> Match_MemberData()
             yield return (@"(ver\.? |[_ ]+)?\d+(\.\d+){2,3}$", " Ver 2.0", RegexOptions.IgnoreCase, 0, 8, false, "");
             yield return (@"(?:|a)?(?:\b\d){2,}", " a 0", RegexOptions.None, 0, 4, false, "");
             yield return (@"(?:|a)?(\d){2,}", " a00a", RegexOptions.None, 0, 5, true, "a00");
+            yield return (@"^( |  )?((\w\d){3,}){3,}", " 12345678901234567", RegexOptions.None, 0, 18, false, "");
+            yield return (@"^( |  )?((\w\d){3,}){3,}", " 123456789012345678", RegexOptions.None, 0, 19, true, " 123456789012345678");
+            yield return (@"^( |  )?((\w\d){3,}){3,}", "  123456789012345678", RegexOptions.None, 0, 20, true, "  123456789012345678");
+            yield return (@"^( |  )?((\w\d){3,}){3,}", "   123456789012345678", RegexOptions.None, 0, 21, false, "");
 
             // Using beginning/end of string chars \A, \Z: Actual - "\\Aaaa\\w+zzz\\Z"
             yield return (@"\Aaaa\w+zzz\Z", "aaaasdfajsdlfjzzz", RegexOptions.IgnoreCase, 0, 17, true, "aaaasdfajsdlfjzzz");