diff --git a/apis/v1alpha2/validation/httproute.go b/apis/v1alpha2/validation/httproute.go
index 70a3c0254b..309f91b49e 100644
--- a/apis/v1alpha2/validation/httproute.go
+++ b/apis/v1alpha2/validation/httproute.go
@@ -17,6 +17,9 @@ limitations under the License.
 package validation
 
 import (
+	"fmt"
+	"strings"
+
 	"k8s.io/apimachinery/pkg/util/validation/field"
 
 	gatewayv1a2 "sigs.k8s.io/gateway-api/apis/v1alpha2"
@@ -28,6 +31,9 @@ var (
 	repeatableHTTPRouteFilters = []gatewayv1a2.HTTPRouteFilterType{
 		gatewayv1a2.HTTPRouteFilterExtensionRef,
 	}
+
+	invalidPathSequences = []string{"//", "/./", "/../", "%2f", "%2F", "#"}
+	invalidPathSuffixes  = []string{"/..", "/."}
 )
 
 // ValidateHTTPRoute validates HTTPRoute according to the Gateway API specification.
@@ -93,3 +99,41 @@ func validateHTTPBackendUniqueFilters(ref []gatewayv1a2.HTTPBackendRef, path *fi
 	}
 	return errs
 }
+
+// webhook validation of HTTPPathMatch
+func validateHTTPPathMatch(path *gatewayv1a2.HTTPPathMatch, fldPath *field.Path) field.ErrorList {
+	allErrs := field.ErrorList{}
+
+	if path.Type == nil {
+		return append(allErrs, field.Required(fldPath.Child("pathType"), "pathType must be specified"))
+	}
+
+	if path.Value == nil {
+		return append(allErrs, field.Required(fldPath.Child("pathValue"), "pathValue must not be nil."))
+	}
+
+	switch *path.Type {
+	case gatewayv1a2.PathMatchExact, gatewayv1a2.PathMatchPrefix:
+		if !strings.HasPrefix(*path.Value, "/") {
+			allErrs = append(allErrs, field.Invalid(fldPath.Child("path"), path, "must be an absolute path"))
+		}
+		if len(*path.Value) > 0 {
+			for _, invalidSeq := range invalidPathSequences {
+				if strings.Contains(*path.Value, invalidSeq) {
+					allErrs = append(allErrs, field.Invalid(fldPath.Child("path"), path, fmt.Sprintf("must not contain '%s'", invalidSeq)))
+				}
+			}
+
+			for _, invalidSuff := range invalidPathSuffixes {
+				if strings.HasSuffix(*path.Value, invalidSuff) {
+					allErrs = append(allErrs, field.Invalid(fldPath.Child("path"), path, fmt.Sprintf("cannot end with '%s'", invalidSuff)))
+				}
+			}
+		}
+	case gatewayv1a2.PathMatchRegularExpression:
+	default:
+		pathTypes := []string{string(gatewayv1a2.PathMatchExact), string(gatewayv1a2.PathMatchPrefix), string(gatewayv1a2.PathMatchRegularExpression)}
+		allErrs = append(allErrs, field.NotSupported(fldPath.Child("pathType"), *path.Type, pathTypes))
+	}
+	return allErrs
+}
diff --git a/apis/v1alpha2/validation/httproute_test.go b/apis/v1alpha2/validation/httproute_test.go
index 26ef140f26..ba1ce76b9f 100644
--- a/apis/v1alpha2/validation/httproute_test.go
+++ b/apis/v1alpha2/validation/httproute_test.go
@@ -390,3 +390,44 @@ func TestValidateHTTPBackendUniqueFilters(t *testing.T) {
 		})
 	}
 }
+
+func TestValidateHTTPPathMatch(t *testing.T) {
+	tests := []struct {
+		name     string
+		path     *gatewayv1a2.HTTPPathMatch
+		errCount int
+	}{
+		{
+			name: "invalid httpRoute prefix",
+			path: &gatewayv1a2.HTTPPathMatch{
+				Type:  pkgutils.PathMatchTypePtr("Prefix"),
+				Value: utilpointer.String("/."),
+			},
+			errCount: 1,
+		},
+		{
+			name: "invalid httpRoute Exact",
+			path: &gatewayv1a2.HTTPPathMatch{
+				Type:  pkgutils.PathMatchTypePtr("Exact"),
+				Value: utilpointer.String("/foo/./bar"),
+			},
+			errCount: 1,
+		},
+		{
+			name: "invalid httpRoute prefix",
+			path: &gatewayv1a2.HTTPPathMatch{
+				Type:  pkgutils.PathMatchTypePtr("Prefix"),
+				Value: utilpointer.String("/"),
+			},
+			errCount: 0,
+		},
+	}
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			errs := validateHTTPPathMatch(tc.path, field.NewPath("spec").Child("rules").Child("matches").Child("path"))
+			if len(errs) != tc.errCount {
+				t.Errorf("TestValidateHTTPPathMatch() got %v errors, want %v errors", len(errs), tc.errCount)
+			}
+		})
+	}
+}