diff --git a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexInterpreter.cs b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexInterpreter.cs
index 4cc3dc528605b9..cfe5e9859ed61e 100644
--- a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexInterpreter.cs
+++ b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexInterpreter.cs
@@ -20,6 +20,7 @@ internal sealed class RegexInterpreter : RegexRunner
         private int _codepos;
         private bool _rightToLeft;
         private bool _caseInsensitive;
+        private int _maxBacktrackPosition = -1;
 
         public RegexInterpreter(RegexCode code, CultureInfo culture)
         {
@@ -214,6 +215,23 @@ private char Forwardcharnext()
             return _caseInsensitive ? _textInfo.ToLower(ch) : ch;
         }
 
+        private void OptimizeRuntextposBacktracking(string str)
+        {
+            // If called after a greedy op such as a .*, we would have zipped runtextpos to the end without really examining any characters. Reset to maxBacktrackPos here as an optimization
+            if (_maxBacktrackPosition != -1 && runtextpos > _maxBacktrackPosition)
+            {
+                // If lastIndexOf is -1, we backtrack to the max extent possible.
+                runtextpos = _maxBacktrackPosition;
+                ReadOnlySpan<char> runtextSpan = runtext.AsSpan(_maxBacktrackPosition);
+                int lastIndexOf = runtextSpan.LastIndexOf(str);
+                if (lastIndexOf > -1)
+                {
+                    // Found the next position to match. Move runtextpos here
+                    runtextpos = _maxBacktrackPosition + lastIndexOf;
+                }
+            }
+        }
+
         private bool MatchString(string str)
         {
             int c = str.Length;
@@ -223,6 +241,7 @@ private bool MatchString(string str)
             {
                 if (runtextend - runtextpos < c)
                 {
+                    OptimizeRuntextposBacktracking(str);
                     return false;
                 }
 
@@ -1026,8 +1045,10 @@ protected override void Go()
                         continue;
 
                     case RegexCode.One:
-                        if (Forwardchars() < 1 || Forwardcharnext() != (char)Operand(0))
+                        char chOne = (char)Operand(0);
+                        if (Forwardchars() < 1 || Forwardcharnext() != chOne)
                         {
+                            OptimizeRuntextposBacktracking(chOne.ToString());
                             break;
                         }
                         advance = 1;
@@ -1185,6 +1206,7 @@ protected override void Go()
                             int len = Math.Min(Operand(1), Forwardchars());
                             char ch = (char)Operand(0);
                             int i;
+                            int tempMaxBacktrackPosition = runtextpos;
 
                             if (!_rightToLeft && !_caseInsensitive)
                             {
@@ -1217,6 +1239,8 @@ protected override void Go()
                             if (len > i && _operator == RegexCode.Notoneloop)
                             {
                                 TrackPush(len - i - 1, runtextpos - Bump());
+                                Debug.Assert(_maxBacktrackPosition == -1, $"maxBacktrackPosition = {_maxBacktrackPosition}, runtext = {runtext}, runtextpos = {runtextpos}, ch = {ch}, code = {_code}, runregex = {runregex}");
+                                _maxBacktrackPosition = tempMaxBacktrackPosition;
                             }
                         }
                         advance = 2;
@@ -1261,6 +1285,16 @@ protected override void Go()
                         {
                             int i = TrackPeek();
                             int pos = TrackPeek(1);
+                            if (_maxBacktrackPosition != -1 && pos > _maxBacktrackPosition && runtextpos < pos && _operator == (RegexCode.Notoneloop | RegexCode.Back) && !_rightToLeft)
+                            {
+                                // The Multi node has bumped us along already
+                                int difference = pos - _maxBacktrackPosition;
+                                Debug.Assert(difference > 0);
+                                pos = runtextpos;
+                                i -= difference;
+                                // We shouldn't be backtracking anymore.
+                                _maxBacktrackPosition = -1;
+                            }
                             runtextpos = pos;
                             if (i > 0)
                             {
diff --git a/src/libraries/System.Text.RegularExpressions/tests/Regex.Match.Tests.cs b/src/libraries/System.Text.RegularExpressions/tests/Regex.Match.Tests.cs
index d2cd6b4e3e1a70..f9eaa966caf543 100644
--- a/src/libraries/System.Text.RegularExpressions/tests/Regex.Match.Tests.cs
+++ b/src/libraries/System.Text.RegularExpressions/tests/Regex.Match.Tests.cs
@@ -204,6 +204,7 @@ public static IEnumerable<object[]> Match_Basic_TestData()
 
             // Using *, +, ?, {}: Actual - "a+\\.?b*\\.?c{2}"
             yield return new object[] { @"a+\.?b*\.+c{2}", "ab.cc", RegexOptions.None, 0, 5, true, "ab.cc" };
+            yield return new object[] { @"[^a]+\.[^z]+", "zzzzz", RegexOptions.None, 0, 5, false, string.Empty };
 
             // RightToLeft
             yield return new object[] { @"\s+\d+", "sdf 12sad", RegexOptions.RightToLeft, 0, 9, true, " 12" };