diff --git a/TUnit.Assertions.UnitTests/StringRegexAssertionTests.cs b/TUnit.Assertions.UnitTests/StringRegexAssertionTests.cs
new file mode 100644
index 0000000000..f1024a42a1
--- /dev/null
+++ b/TUnit.Assertions.UnitTests/StringRegexAssertionTests.cs
@@ -0,0 +1,286 @@
+using System.Text.RegularExpressions;
+using TUnit.Assertions.Extensions;
+
+namespace TUnit.Assertions.UnitTests;
+
+public partial class StringRegexAssertionTests 
+{
+    
+    #region Matches Succeeds
+    [Test]
+    public async Task Matches_WithValidPattern_StringPattern_Succeeds()
+    {
+        var text = "Hello123World";
+        var pattern = @"\w+\d+\w+";
+
+        await TUnitAssert.That(text).Matches(pattern);
+    }
+
+    [Test]
+    public async Task Matches_WithValidPattern_RegexPattern_Succeeds() 
+    {
+        var text = "Hello123World";
+        var pattern = new Regex(@"\w+\d+\w+");
+        
+        await TUnitAssert.That(text).Matches(pattern);
+    }
+
+    #if NET // Needed because NetFramework doesn't support partial methods
+    [GeneratedRegex(@"\w+\d+\w+")]
+    private static partial Regex FindHello123WorldRegex();
+
+    [Test]
+    public async Task Matches_WithValidPattern_GeneratedRegexPattern_Succeeds() 
+    {
+        var text = "Hello123World";
+        Regex regex = FindHello123WorldRegex();
+        
+        await TUnitAssert.That(text).Matches(regex);
+    }
+    #endif
+    #endregion
+    
+    #region Matches Throws
+    [Test]
+    #if NET
+    [TestCase(typeof(RegexParseException), @"[", null!)] // invalid regex
+    #endif 
+    [TestCase(typeof(ArgumentNullException), @"^\d+$", null)]
+    [TestCase(typeof(TUnitAssertionException), @"^\d+$", "Hello123World")]
+    public void Matches_WithInvalidPattern_StringPattern_Throws(Type exceptionType, string pattern, string? text) 
+    {
+        AsyncTestDelegate action = async () => await TUnitAssert.That(text).Matches(pattern);
+
+        Exception? exception = NUnitAssert.ThrowsAsync(exceptionType,action);
+        if (exceptionType != typeof(TUnitAssertionException)) 
+        {
+            return;
+        }
+        
+        NUnitAssert.That(exception!.Message, Is.EqualTo(
+            $"""
+             Expected text match pattern
+
+             but The regex "^\d+$" does not match with "{text}"
+
+             at Assert.That(text).Matches(pattern)
+             """
+        ));
+    }
+    
+    [Test]
+    [TestCase(typeof(ArgumentNullException), null)]
+    [TestCase(typeof(TUnitAssertionException), "Hello123World")]
+    public void Matches_WithInvalidPattern_RegexPattern_Throws(Type exceptionType, string? text) 
+    {
+        var pattern = new Regex(@"^\d+$");
+        
+        AsyncTestDelegate action = async () => await TUnitAssert.That(text).Matches(pattern); 
+
+        var exception = NUnitAssert.ThrowsAsync(exceptionType, action);
+        if (exceptionType != typeof(TUnitAssertionException)) 
+        {
+            return;
+        }
+
+        NUnitAssert.That(exception!.Message, Is.EqualTo(
+            $"""
+             Expected text match pattern
+
+             but The regex "^\d+$" does not match with "{text}"
+
+             at Assert.That(text).Matches(pattern)
+             """
+        ));
+    }
+    
+    #if NET // Needed because NetFramework doesn't support partial methods
+    [GeneratedRegex(@"^\d+$")]
+    private static partial Regex Matches_FindNumberRegex();
+    
+    [Test]
+    [TestCase(typeof(ArgumentNullException), null)]
+    [TestCase(typeof(TUnitAssertionException), "Hello123World")]
+    public void Matches_WithInvalidPattern_GeneratedRegexPattern_Throws(Type exceptionType, string? text) 
+    {
+        Regex regex = Matches_FindNumberRegex();
+        
+        AsyncTestDelegate action = async () => await TUnitAssert.That(text).Matches(regex);
+
+        Exception? exception = NUnitAssert.ThrowsAsync(exceptionType, action);
+        if (exceptionType != typeof(TUnitAssertionException)) 
+        {
+            return;
+        }
+        
+        NUnitAssert.That(exception!.Message, Is.EqualTo(
+            $"""
+             Expected text match regex
+             
+             but The regex "^\d+$" does not match with "Hello123World"
+             
+             at Assert.That(text).Matches(regex)
+             """
+        ));
+    }
+    #endif
+    
+    [Test]
+    [TestCase(typeof(RegexMatchTimeoutException), "(a+)+$", "aaaaaaaaaaaaaaaaaaaaaaaaaaaaaa!")]
+    [TestCase(typeof(RegexMatchTimeoutException), @"^(([a-z])+.)+[A-Z]([a-z])+$", "aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa!")]
+    public void Matches_WithTimeoutPattern_Throws(Type exceptionType, string pattern, string text)
+    {
+        // Create regex with a short timeout
+        #if NET8_0_OR_GREATER
+            var timeout = TimeSpan.FromMicroseconds(1);
+        #else
+            var timeout = TimeSpan.FromTicks(1);
+        #endif
+        var regex = new Regex(pattern, RegexOptions.None, timeout);
+    
+        AsyncTestDelegate action = async () => await TUnitAssert.That(text).Matches(regex);
+
+        var exception = NUnitAssert.ThrowsAsync<RegexMatchTimeoutException>(action);
+        NUnitAssert.That(exception!.Pattern, Is.EqualTo(pattern));
+    }
+    #endregion
+    
+    #region DoesNotMatch Succeeds
+    [Test]
+    public async Task DoesNotMatch_WithValidPattern_StringPattern_Succeeds()
+    {
+        var text = "Hello123World";
+        var pattern = @"^\d+$";
+
+        await TUnitAssert.That(text).DoesNotMatch(pattern);
+    }
+
+    [Test]
+    public async Task DoesNotMatch_WithValidPattern_RegexPattern_Succeeds() 
+    {
+        var text = "Hello123World";
+        var pattern = new Regex(@"^\d+$");
+        
+        await TUnitAssert.That(text).DoesNotMatch(pattern);
+    }
+
+    #if NET // Needed because NetFramework doesn't support partial methods
+    [GeneratedRegex(@"^\d+$")]
+    private static partial Regex DoesNotMatch_FindNumberOnlyRegex();
+
+    [Test]
+    public async Task DoesNotMatch_WithValidPattern_GeneratedRegexPattern_Succeeds() 
+    {
+        var text = "Hello123World";
+        Regex regex = DoesNotMatch_FindNumberOnlyRegex();
+        
+        await TUnitAssert.That(text).DoesNotMatch(regex);
+    }
+    #endif
+    #endregion
+
+    #region DoesNotMatch Throws
+    [Test]
+    #if NET
+    [TestCase(typeof(RegexParseException), @"[", null!)] // invalid regex
+    #endif 
+    [TestCase(typeof(ArgumentNullException), @"^\d+$", null)]
+    [TestCase(typeof(TUnitAssertionException), @"^\d+$", "123")]
+    public void DoesNotMatch_WithInvalidPattern_StringPattern_Throws(Type exceptionType, string pattern, string? text) 
+    {
+        AsyncTestDelegate action = async () => await TUnitAssert.That(text).DoesNotMatch(pattern);
+
+        Exception? exception = NUnitAssert.ThrowsAsync(exceptionType, action);
+        if (exceptionType != typeof(TUnitAssertionException)) 
+        {
+            return;
+        }
+        
+        NUnitAssert.That(exception!.Message, Is.EqualTo(
+            $"""
+             Expected text to not match with pattern
+             
+             but The regex "^\d+$" matches with "{text}"
+             
+             at Assert.That(text).DoesNotMatch(pattern)
+             """
+        ));
+    }
+
+    [Test]
+    [TestCase(typeof(ArgumentNullException), null)]
+    [TestCase(typeof(TUnitAssertionException), "123")]
+    public void DoesNotMatch_WithInvalidPattern_RegexPattern_Throws(Type exceptionType, string? text) 
+    {
+        var pattern = new Regex(@"^\d+$");
+        
+        AsyncTestDelegate action = async () => await TUnitAssert.That(text).DoesNotMatch(pattern);
+
+        Exception? exception = NUnitAssert.ThrowsAsync(exceptionType, action);
+        if (exceptionType != typeof(TUnitAssertionException)) 
+        {
+            return;
+        }
+        
+        NUnitAssert.That(exception!.Message, Is.EqualTo(
+            $"""
+             Expected text to not match with pattern
+             
+             but The regex "^\d+$" matches with "{text}"
+             
+             at Assert.That(text).DoesNotMatch(pattern)
+             """
+        ));
+    }
+
+    #if NET // Needed because NetFramework doesn't support partial methods
+    [GeneratedRegex(@"^\d+$")]
+    private static partial Regex FindNumberRegex();
+
+    [Test]
+    [TestCase(typeof(ArgumentNullException), null)]
+    [TestCase(typeof(TUnitAssertionException), "123")]
+    public void DoesNotMatch_WithInvalidPattern_GeneratedRegexPattern_Throws(Type exceptionType, string? text) 
+    {
+        Regex regex = FindNumberRegex();
+        
+        AsyncTestDelegate action = async () => await TUnitAssert.That(text).DoesNotMatch(regex);
+
+        Exception? exception = NUnitAssert.ThrowsAsync(exceptionType, action);
+        if (exceptionType != typeof(TUnitAssertionException)) 
+        {
+            return;
+        }
+        
+        NUnitAssert.That(exception!.Message, Is.EqualTo(
+            $"""
+             Expected text to not match with regex
+             
+             but The regex "^\d+$" matches with "{text}"
+             
+             at Assert.That(text).DoesNotMatch(regex)
+             """
+        ));
+    }
+    #endif
+    
+    [Test]
+    [TestCase(typeof(RegexMatchTimeoutException), "(a+)+$", "aaaaaaaaaaaaaaaaaaaaaaaaaaaaaa!")]
+    [TestCase(typeof(RegexMatchTimeoutException), @"^(([a-z])+.)+[A-Z]([a-z])+$", "aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa!")]
+    public void DoesNotMatch_WithTimeoutPattern_Throws(Type exceptionType, string pattern, string text)
+    {
+        // Create regex with a short timeout
+        #if NET8_0_OR_GREATER
+            var timeout = TimeSpan.FromMicroseconds(1);
+        #else
+            var timeout = TimeSpan.FromTicks(1);
+        #endif
+        var regex = new Regex(pattern, RegexOptions.None, timeout);
+    
+        AsyncTestDelegate action = async () => await TUnitAssert.That(text).DoesNotMatch(regex);
+
+        var exception = NUnitAssert.ThrowsAsync<RegexMatchTimeoutException>(action);
+        NUnitAssert.That(exception!.Pattern, Is.EqualTo(pattern));
+    }
+    #endregion
+}
\ No newline at end of file
diff --git a/TUnit.Assertions/Assertions/Strings/DoesNotExtensions_String.cs b/TUnit.Assertions/Assertions/Strings/DoesNotExtensions_String.cs
index 2bfe0d24ac..d3b1388d53 100644
--- a/TUnit.Assertions/Assertions/Strings/DoesNotExtensions_String.cs
+++ b/TUnit.Assertions/Assertions/Strings/DoesNotExtensions_String.cs
@@ -1,6 +1,7 @@
 #nullable disable
 
 using System.Runtime.CompilerServices;
+using System.Text.RegularExpressions;
 using TUnit.Assertions.AssertConditions;
 using TUnit.Assertions.AssertConditions.Interfaces;
 using TUnit.Assertions.AssertConditions.String;
@@ -57,4 +58,22 @@ public static InvokableValueAssertionBuilder<string> DoesNotEndWith(this IValueS
             $"not end with {expected}")
             , [doNotPopulateThisValue1, doNotPopulateThisValue2]);
     }
+    
+    public static InvokableValueAssertionBuilder<string> DoesNotMatch(this IValueSource<string> valueSource, string regex, [CallerArgumentExpression(nameof(regex))] string expression = "")
+    {
+        return DoesNotMatch(valueSource, new Regex(regex), expression);
+    }
+    
+    public static InvokableValueAssertionBuilder<string> DoesNotMatch(this IValueSource<string> valueSource, Regex regex, [CallerArgumentExpression(nameof(regex))] string expression = "")
+    {
+        return valueSource.RegisterAssertion(new FuncValueAssertCondition<string, Regex>(regex,
+                (actual, _, _) =>
+                {
+                    Verify.ArgNotNull(actual);
+                    return !regex.IsMatch(actual);
+                },
+                (actual, _, _) => $"The regex \"{regex}\" matches with \"{actual}\"",
+                $"to not match with {expression}")
+            , [expression]);
+    }
 }
\ No newline at end of file
diff --git a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet2_0.verified.txt b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet2_0.verified.txt
index 56f334157b..57e3cdf3fa 100644
--- a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet2_0.verified.txt
+++ b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet2_0.verified.txt
@@ -1276,6 +1276,8 @@ namespace TUnit.Assertions.Extensions
             where TDictionary : System.Collections.IDictionary { }
         public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotEndWith(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string expected, [System.Runtime.CompilerServices.CallerArgumentExpression("expected")] string doNotPopulateThisValue = null) { }
         public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotEndWith(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string expected, System.StringComparison stringComparison, [System.Runtime.CompilerServices.CallerArgumentExpression("expected")] string doNotPopulateThisValue1 = null, [System.Runtime.CompilerServices.CallerArgumentExpression("stringComparison")] string doNotPopulateThisValue2 = null) { }
+        public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotMatch(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, System.Text.RegularExpressions.Regex regex, [System.Runtime.CompilerServices.CallerArgumentExpression("regex")] string expression = "") { }
+        public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotMatch(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string regex, [System.Runtime.CompilerServices.CallerArgumentExpression("regex")] string expression = "") { }
         public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotStartWith(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string expected, [System.Runtime.CompilerServices.CallerArgumentExpression("expected")] string doNotPopulateThisValue = null) { }
         public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotStartWith(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string expected, System.StringComparison stringComparison, [System.Runtime.CompilerServices.CallerArgumentExpression("expected")] string doNotPopulateThisValue1 = null, [System.Runtime.CompilerServices.CallerArgumentExpression("stringComparison")] string doNotPopulateThisValue2 = null) { }
     }
diff --git a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet8_0.verified.txt b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet8_0.verified.txt
index 61606353a0..7754daa620 100644
--- a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet8_0.verified.txt
+++ b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet8_0.verified.txt
@@ -1315,6 +1315,8 @@ namespace TUnit.Assertions.Extensions
             where TDictionary : System.Collections.IDictionary { }
         public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotEndWith(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string expected, [System.Runtime.CompilerServices.CallerArgumentExpression("expected")] string doNotPopulateThisValue = null) { }
         public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotEndWith(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string expected, System.StringComparison stringComparison, [System.Runtime.CompilerServices.CallerArgumentExpression("expected")] string doNotPopulateThisValue1 = null, [System.Runtime.CompilerServices.CallerArgumentExpression("stringComparison")] string doNotPopulateThisValue2 = null) { }
+        public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotMatch(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, System.Text.RegularExpressions.Regex regex, [System.Runtime.CompilerServices.CallerArgumentExpression("regex")] string expression = "") { }
+        public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotMatch(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string regex, [System.Runtime.CompilerServices.CallerArgumentExpression("regex")] string expression = "") { }
         public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotStartWith(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string expected, [System.Runtime.CompilerServices.CallerArgumentExpression("expected")] string doNotPopulateThisValue = null) { }
         public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotStartWith(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string expected, System.StringComparison stringComparison, [System.Runtime.CompilerServices.CallerArgumentExpression("expected")] string doNotPopulateThisValue1 = null, [System.Runtime.CompilerServices.CallerArgumentExpression("stringComparison")] string doNotPopulateThisValue2 = null) { }
     }
diff --git a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet9_0.verified.txt b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet9_0.verified.txt
index 125937f509..fb242b5c03 100644
--- a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet9_0.verified.txt
+++ b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet9_0.verified.txt
@@ -1315,6 +1315,8 @@ namespace TUnit.Assertions.Extensions
             where TDictionary : System.Collections.IDictionary { }
         public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotEndWith(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string expected, [System.Runtime.CompilerServices.CallerArgumentExpression("expected")] string doNotPopulateThisValue = null) { }
         public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotEndWith(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string expected, System.StringComparison stringComparison, [System.Runtime.CompilerServices.CallerArgumentExpression("expected")] string doNotPopulateThisValue1 = null, [System.Runtime.CompilerServices.CallerArgumentExpression("stringComparison")] string doNotPopulateThisValue2 = null) { }
+        public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotMatch(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, System.Text.RegularExpressions.Regex regex, [System.Runtime.CompilerServices.CallerArgumentExpression("regex")] string expression = "") { }
+        public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotMatch(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string regex, [System.Runtime.CompilerServices.CallerArgumentExpression("regex")] string expression = "") { }
         public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotStartWith(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string expected, [System.Runtime.CompilerServices.CallerArgumentExpression("expected")] string doNotPopulateThisValue = null) { }
         public static TUnit.Assertions.AssertionBuilders.InvokableValueAssertionBuilder<string> DoesNotStartWith(this TUnit.Assertions.AssertConditions.Interfaces.IValueSource<string> valueSource, string expected, System.StringComparison stringComparison, [System.Runtime.CompilerServices.CallerArgumentExpression("expected")] string doNotPopulateThisValue1 = null, [System.Runtime.CompilerServices.CallerArgumentExpression("stringComparison")] string doNotPopulateThisValue2 = null) { }
     }