diff --git a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexRunner.cs b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexRunner.cs
index 2e699c8e85a8d4..4ba1ebb976edb9 100644
--- a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexRunner.cs
+++ b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexRunner.cs
@@ -573,6 +573,13 @@ protected void TransferCapture(int capnum, int uncapnum, int start, int end)
             else if (end <= start2)
             {
                 start = start2;
+
+                // Ensure we don't create a capture with negative length
+                // When the balancing capture precedes the balanced group, end might be less than the new start
+                if (end < start)
+                {
+                    end = start;
+                }
             }
             else
             {
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 f51604442bcfaf..41c1283f690901 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
@@ -2881,5 +2881,196 @@ public async Task MatchNonBacktrackingOver255Minterms()
                 Assert.Equal(272, ms[0].Length);
             }
         }
+
+        /// <summary>
+        /// Tests for balancing groups where the balancing group's captured content
+        /// precedes the position of the group being balanced.
+        /// This tests the fix for https://github.com/dotnet/runtime/issues/111161
+        /// </summary>
+        [Theory]
+        [MemberData(nameof(BalancingGroup_WithConditional_MemberData))]
+        public void BalancingGroup_WithConditional_ConsistentBehavior(Regex regex, string input, bool expectedGroup2Matched, string expectedMatch)
+        {
+            Match m = regex.Match(input);
+
+            Assert.True(m.Success, $"Match should succeed for input '{input}'");
+            Assert.Equal(expectedMatch, m.Value);
+
+#if !NETFRAMEWORK // This bug was fixed in .NET Core and doesn't exist in .NET Framework
+            // Check that the group 2 state is consistent
+            bool group2Success = m.Groups[2].Success;
+            int group2CapturesCount = m.Groups[2].Captures.Count;
+
+            // The key test: Group.Success and Captures.Count should be consistent with the conditional behavior
+            Assert.Equal(expectedGroup2Matched, group2Success);
+            if (expectedGroup2Matched)
+            {
+                Assert.True(group2CapturesCount > 0, "If group 2 matched, it should have at least one capture");
+            }
+            else
+            {
+                Assert.Equal(0, group2CapturesCount);
+            }
+#else
+            // On .NET Framework, just use the parameters to avoid xUnit warning
+            _ = expectedGroup2Matched;
+#endif
+        }
+
+        public static IEnumerable<object[]> BalancingGroup_WithConditional_MemberData()
+        {
+            foreach (RegexEngine engine in RegexHelpers.AvailableEngines)
+            {
+                if (RegexHelpers.IsNonBacktracking(engine))
+                {
+                    // NonBacktracking engine doesn't support balancing groups
+                    continue;
+                }
+
+                var cases = new (string Pattern, string Input, bool ExpectedGroup2Matched, string ExpectedMatch)[]
+                {
+                    // Original bug report pattern
+                    // The balancing group (?'2-1'(?'x1'..)) captures content that comes BEFORE group 1's capture
+                    (@"\d+((?'x'[a-z-[b]]+)).(?<=(?'2-1'(?'x1'..)).{6})b(?(2)(?'Group2Captured'.)|(?'Group2NotCaptured'.))",
+                        "00123xzacvb1", true, "00123xzacvb1"),
+
+                    // Simpler test case: balancing group in forward context (normal case)
+                    (@"(a)(?'2-1'b)(?(2)c|d)", "abc", true, "abc"),
+
+                    // Balancing group in lookbehind where captured content comes after balanced group
+                    (@"(a)b(?<=(?'2-1'.))c(?(2)d|e)", "abcd", true, "abcd"),
+
+                    // Balancing group in lookbehind where captured content comes before balanced group (bug scenario)
+                    (@"a(b)c(?<=(?'2-1'a)..)d(?(2)e|f)", "abcde", true, "abcde"),
+                };
+
+                Regex[] regexes = RegexHelpers.GetRegexes(engine, cases.Select(c => (c.Pattern, (System.Globalization.CultureInfo?)null, (RegexOptions?)null, (TimeSpan?)null)).ToArray());
+                for (int i = 0; i < cases.Length; i++)
+                {
+                    yield return new object[] { regexes[i], cases[i].Input, cases[i].ExpectedGroup2Matched, cases[i].ExpectedMatch };
+                }
+            }
+        }
+
+        /// <summary>
+        /// Tests that IsMatched() behavior is consistent with Group.Success and Group.Captures.Count
+        /// after TidyBalancing is called.
+        /// </summary>
+        [Theory]
+        [MemberData(nameof(BalancingGroup_IsMatched_Consistency_MemberData))]
+        public void BalancingGroup_IsMatched_Consistency(Regex regex, string input, int groupNumber, bool expectedMatched)
+        {
+            Match m = regex.Match(input);
+
+            Assert.True(m.Success, $"Match should succeed for input '{input}'");
+
+#if !NETFRAMEWORK // This bug was fixed in .NET Core and doesn't exist in .NET Framework
+            // Check that the group state is consistent
+            bool groupSuccess = m.Groups[groupNumber].Success;
+            int capturesCount = m.Groups[groupNumber].Captures.Count;
+
+            Assert.Equal(expectedMatched, groupSuccess);
+            if (expectedMatched)
+            {
+                Assert.True(capturesCount > 0, $"If group {groupNumber} matched, it should have at least one capture");
+            }
+            else
+            {
+                Assert.Equal(0, capturesCount);
+            }
+#else
+            // On .NET Framework, just use the parameters to avoid xUnit warning
+            _ = groupNumber;
+            _ = expectedMatched;
+#endif
+        }
+
+        public static IEnumerable<object[]> BalancingGroup_IsMatched_Consistency_MemberData()
+        {
+            foreach (RegexEngine engine in RegexHelpers.AvailableEngines)
+            {
+                if (RegexHelpers.IsNonBacktracking(engine))
+                {
+                    continue;
+                }
+
+                var cases = new (string Pattern, string Input, int GroupNumber, bool ExpectedMatched)[]
+                {
+                    // Group 1 should be balanced out (no captures remaining)
+                    (@"(a)(?'2-1'b)", "ab", 1, false),
+
+                    // Group 2 should have a capture
+                    (@"(a)(?'2-1'b)", "ab", 2, true),
+
+                    // Balancing in lookbehind - group 1 should be balanced out
+                    (@"(a)b(?<=(?'2-1'.))c", "abc", 1, false),
+
+                    // Balancing in lookbehind - group 2 should have a capture
+                    (@"(a)b(?<=(?'2-1'.))c", "abc", 2, true),
+
+                    // Original bug pattern - group 1 should be balanced out
+                    (@"\d+((?'x'[a-z-[b]]+)).(?<=(?'2-1'(?'x1'..)).{6})b", "00123xzacvb", 1, false),
+
+                    // Original bug pattern - group 2 should have a capture
+                    (@"\d+((?'x'[a-z-[b]]+)).(?<=(?'2-1'(?'x1'..)).{6})b", "00123xzacvb", 2, true),
+                };
+
+                Regex[] regexes = RegexHelpers.GetRegexes(engine, cases.Select(c => (c.Pattern, (System.Globalization.CultureInfo?)null, (RegexOptions?)null, (TimeSpan?)null)).ToArray());
+                for (int i = 0; i < cases.Length; i++)
+                {
+                    yield return new object[] { regexes[i], cases[i].Input, cases[i].GroupNumber, cases[i].ExpectedMatched };
+                }
+            }
+        }
+
+        /// <summary>
+        /// Tests various balancing group scenarios to ensure correct behavior.
+        /// </summary>
+        [Theory]
+        [MemberData(nameof(BalancingGroup_Various_MemberData))]
+        public void BalancingGroup_Various_Scenarios(Regex regex, string input, string expectedValue, int expectedGroup1Count, int expectedGroup2Count)
+        {
+            Match m = regex.Match(input);
+
+            Assert.True(m.Success);
+            Assert.Equal(expectedValue, m.Value);
+
+#if !NETFRAMEWORK // This test depends on the fix for balancing groups
+            Assert.Equal(expectedGroup1Count, m.Groups[1].Captures.Count);
+            Assert.Equal(expectedGroup2Count, m.Groups[2].Captures.Count);
+#else
+            // On .NET Framework, just use the parameters to avoid xUnit warning
+            _ = expectedGroup1Count;
+            _ = expectedGroup2Count;
+#endif
+        }
+
+        public static IEnumerable<object[]> BalancingGroup_Various_MemberData()
+        {
+            foreach (RegexEngine engine in RegexHelpers.AvailableEngines)
+            {
+                if (RegexHelpers.IsNonBacktracking(engine))
+                {
+                    continue;
+                }
+
+                var cases = new (string Pattern, string Input, string ExpectedValue, int ExpectedGroup1Count, int ExpectedGroup2Count)[]
+                {
+                    // Basic balancing: group 1 captured, then balanced into group 2
+                    // Creates a zero-length capture in group 2
+                    (@"(a)(?'2-1'b)", "ab", "ab", 0, 1),
+
+                    // Multiple captures: group 2 is the second (a), then balancing transfers from group 1
+                    // Group 2 gets its own capture plus a zero-length capture from balancing
+                    (@"(a)(a)(?'2-1'b)", "aab", "aab", 0, 2),
+                };
+
+                Regex[] regexes = RegexHelpers.GetRegexes(engine, cases.Select(c => (c.Pattern, (System.Globalization.CultureInfo?)null, (RegexOptions?)null, (TimeSpan?)null)).ToArray());
+                for (int i = 0; i < cases.Length; i++)
+                {
+                    yield return new object[] { regexes[i], cases[i].Input, cases[i].ExpectedValue, cases[i].ExpectedGroup1Count, cases[i].ExpectedGroup2Count };
+                }
+            }
+        }
     }
 }