diff --git a/src/Expectation.php b/src/Expectation.php
index b156d558..fcd54a75 100644
--- a/src/Expectation.php
+++ b/src/Expectation.php
@@ -5,6 +5,7 @@ declare(strict_types=1);
 namespace Pest;
 
 use PHPUnit\Framework\Assert;
+use PHPUnit\Framework\Constraint\Constraint;
 
 /**
  * @internal
@@ -504,6 +505,16 @@ final class Expectation
         return $this;
     }
 
+    /**
+     * Asserts that the value matches a constraint.
+     */
+    public function toMatchConstraint(Constraint $constraint): Expectation
+    {
+        Assert::assertThat($this->value, $constraint);
+
+        return $this;
+    }
+
     /**
      * Dynamically calls methods on the class without any arguments.
      *
diff --git a/tests/Expect/toMatchConstraint.php b/tests/Expect/toMatchConstraint.php
new file mode 100644
index 00000000..e5b4b681
--- /dev/null
+++ b/tests/Expect/toMatchConstraint.php
@@ -0,0 +1,16 @@
+<?php
+
+use PHPUnit\Framework\Constraint\IsTrue;
+use PHPUnit\Framework\ExpectationFailedException;
+
+test('pass', function () {
+    expect(true)->toMatchConstraint(new IsTrue());
+});
+
+test('failures', function () {
+    expect(false)->toMatchConstraint(new IsTrue());
+})->throws(ExpectationFailedException::class);
+
+test('not failures', function () {
+    expect(true)->not->toMatchConstraint(new IsTrue());
+})->throws(ExpectationFailedException::class);