diff --git a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexNode.cs b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexNode.cs
index 3dce343ea8867a..de8df332e36359 100644
--- a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexNode.cs
+++ b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexNode.cs
@@ -2096,8 +2096,10 @@ private RegexNode ReduceLookaround()
             Debug.Assert(ChildCount() == 1);
 
             // Captures inside of negative lookarounds are undone after the lookaround. Thus, if there's nothing
-            // inside of the negative lookaround that needs that capture group (namely a backreference), we can
-            // remove the capture.
+            // inside of the negative lookaround that relies on or impacts persisted state, we can remove the capture.
+            // This includes backreferences (because backreferences within the lookaround still need to refer to that
+            // capture group) and balancing groups (because they can impact and are impacted by capture stacks from
+            // captures outside of the lookaround).
             if (Kind is RegexNodeKind.NegativeLookaround && ContainsKind(Child(0), [RegexNodeKind.Backreference, RegexNodeKind.BackreferenceConditional]) is false)
             {
                 if (RemoveCaptures(this, 0))
@@ -2111,7 +2113,9 @@ static bool RemoveCaptures(RegexNode parent, int nodeIndex)
                 {
                     RegexNode node = parent.Child(nodeIndex);
 
-                    if (node.Kind is RegexNodeKind.Capture)
+                    // Only remove captures that don't rely on or impact persisted state.
+                    // Balancing groups (N != -1) impact capture stacks and must be preserved.
+                    if (node is { Kind: RegexNodeKind.Capture, N: -1 })
                     {
                         parent.ReplaceChild(nodeIndex, node.Child(0));
                         RemoveCaptures(parent, nodeIndex);
diff --git a/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.Count.Tests.cs b/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.Count.Tests.cs
index d568aa2027406f..76fa7713faab68 100644
--- a/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.Count.Tests.cs
+++ b/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.Count.Tests.cs
@@ -90,6 +90,9 @@ public static IEnumerable<object[]> Count_ReturnsExpectedCount_TestData()
                     yield return new object[] { engine, @"\b\w+\b", "abc def ghi jkl", 15, RegexOptions.RightToLeft, 4 };
                     yield return new object[] { RegexEngine.Interpreter, @"(?<=abc)\w", "abcxabcy", 8, RegexOptions.RightToLeft, 2 };
                     yield return new object[] { engine, @"(?<=abc)\w", "abcxabcy", 7, RegexOptions.RightToLeft, 1 };
+
+                    // Balancing groups in negative lookarounds should not be removed
+                    yield return new object[] { engine, @"()(?'-1')(?!(?'-1'))", "abc", 0, RegexOptions.None, 4 };
                 }
             }
         }
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 01553e0659b850..f0622cb83d360c 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
@@ -649,6 +649,11 @@ public static IEnumerable<object[]> Match_MemberData()
                 yield return (@"(?<cat>cat)\w+(?<dog-0>dog)", "cat_Hello_World_dog", RegexOptions.None, 0, 19, false, string.Empty);
                 yield return (@"(.)(?'2-1'(?'-1'))", "cat", RegexOptions.None, 0, 3, false, string.Empty);
                 yield return (@"(?'2-1'(.))", "cat", RegexOptions.None, 0, 3, true, "c");
+
+                // Balancing groups in negative lookarounds should not be removed
+                // The pattern captures group 1, uncaptures it, then checks the negative lookahead
+                // The negative lookahead contains a balancing group that should not be removed
+                yield return (@"()(?'-1')(?!(?'-1'))", "a", RegexOptions.None, 0, 1, true, string.Empty);
             }
 
             // Atomic Zero-Width Assertions \A \Z \z \b \B