diff --git a/internal/nginx/config/generator.go b/internal/nginx/config/generator.go
index ce2937501f..77d5236eef 100644
--- a/internal/nginx/config/generator.go
+++ b/internal/nginx/config/generator.go
@@ -4,6 +4,7 @@ import (
 	"encoding/json"
 	"errors"
 	"fmt"
+	"strings"
 
 	"k8s.io/apimachinery/pkg/types"
 	"sigs.k8s.io/gateway-api/apis/v1alpha2"
@@ -193,11 +194,18 @@ func createHTTPMatch(match v1alpha2.HTTPRouteMatch, redirectPath string) httpMat
 
 	if match.Headers != nil {
 		headers := make([]string, 0, len(match.Headers))
+		headerNames := make(map[string]struct{})
 
 		// FIXME(kate-osborn): For now we only support type "Exact".
 		for _, h := range match.Headers {
 			if *h.Type == v1alpha2.HeaderMatchExact {
-				headers = append(headers, createHeaderKeyValString(h))
+				// duplicate header names are not permitted by the spec
+				// only configure the first entry for every header name (case-insensitive)
+				lowerName := strings.ToLower(string(h.Name))
+				if _, ok := headerNames[lowerName]; !ok {
+					headers = append(headers, createHeaderKeyValString(h))
+					headerNames[lowerName] = struct{}{}
+				}
 			}
 		}
 		hm.Headers = headers
diff --git a/internal/nginx/config/generator_test.go b/internal/nginx/config/generator_test.go
index 0b698b539b..a27630195b 100644
--- a/internal/nginx/config/generator_test.go
+++ b/internal/nginx/config/generator_test.go
@@ -640,6 +640,16 @@ func TestCreateHTTPMatch(t *testing.T) {
 			Value: "val-3",
 		},
 	}
+
+	testDuplicateHeaders := make([]v1alpha2.HTTPHeaderMatch, 0, 5)
+	duplicateHeaderMatch := v1alpha2.HTTPHeaderMatch{
+		Type:  helpers.GetHeaderMatchTypePointer(v1alpha2.HeaderMatchExact),
+		Name:  "HEADER-2", // header names are case-insensitive
+		Value: "val-2",
+	}
+	testDuplicateHeaders = append(testDuplicateHeaders, testHeaderMatches...)
+	testDuplicateHeaders = append(testDuplicateHeaders, duplicateHeaderMatch)
+
 	testQueryParamMatches := []v1alpha2.HTTPQueryParamMatch{
 		{
 			Type:  helpers.GetQueryParamMatchTypePointer(v1alpha2.QueryParamMatchExact),
@@ -763,6 +773,16 @@ func TestCreateHTTPMatch(t *testing.T) {
 			},
 			msg: "method, headers, and query params match",
 		},
+		{
+			match: v1alpha2.HTTPRouteMatch{
+				Headers: testDuplicateHeaders,
+			},
+			expected: httpMatch{
+				Headers:      expectedHeaders,
+				RedirectPath: testPath,
+			},
+			msg: "duplicate header names",
+		},
 	}
 	for _, tc := range tests {
 		result := createHTTPMatch(tc.match, testPath)
diff --git a/internal/nginx/modules/src/httpmatches.js b/internal/nginx/modules/src/httpmatches.js
index 56adf29415..2ff435196d 100644
--- a/internal/nginx/modules/src/httpmatches.js
+++ b/internal/nginx/modules/src/httpmatches.js
@@ -129,8 +129,6 @@ function testMatch(r, match) {
   return true;
 }
 
-// FIXME(osborn): Need to add special handling for repeated headers.
-// Should follow guidance from https://www.rfc-editor.org/rfc/rfc7230.html#section-3.2.2.
 function headersMatch(requestHeaders, headers) {
   for (let i = 0; i < headers.length; i++) {
     const h = headers[i];
@@ -144,7 +142,13 @@ function headersMatch(requestHeaders, headers) {
     // This means that requestHeaders['FOO'] is equivalent to requestHeaders['foo'].
     let val = requestHeaders[kv[0]];
 
-    if (!val || val !== kv[1]) {
+    if (!val) {
+      return false;
+    }
+
+    // split on comma because nginx uses commas to delimit multiple header values
+    const values = val.split(',');
+    if (!values.includes(kv[1])) {
       return false;
     }
   }
diff --git a/internal/nginx/modules/test/httpmatches.test.js b/internal/nginx/modules/test/httpmatches.test.js
index cb7a6c7550..eec8199b1a 100644
--- a/internal/nginx/modules/test/httpmatches.test.js
+++ b/internal/nginx/modules/test/httpmatches.test.js
@@ -253,6 +253,14 @@ describe('headersMatch', () => {
       },
       expected: true,
     },
+    {
+      name: 'returns true if request has multiple values for a header name and one value matches ',
+      headers: ['multiValueHeader:val3'],
+      requestHeaders: {
+        multiValueHeader: 'val1,val2,val3,val4,val5',
+      },
+      expected: true,
+    },
   ];
 
   tests.forEach((test) => {