diff --git a/pkg/middlewares/retry/retry.go b/pkg/middlewares/retry/retry.go
index e1eee533d..5c95486d3 100644
--- a/pkg/middlewares/retry/retry.go
+++ b/pkg/middlewares/retry/retry.go
@@ -196,6 +196,9 @@ func (r *responseWriterWithoutCloseNotify) Write(buf []byte) (int, error) {
 	if r.ShouldRetry() {
 		return len(buf), nil
 	}
+	if !r.written {
+		r.WriteHeader(http.StatusOK)
+	}
 	return r.responseWriter.Write(buf)
 }
 
diff --git a/pkg/middlewares/retry/retry_test.go b/pkg/middlewares/retry/retry_test.go
index be2606ce4..8d493cf11 100644
--- a/pkg/middlewares/retry/retry_test.go
+++ b/pkg/middlewares/retry/retry_test.go
@@ -169,7 +169,6 @@ func TestRetryListeners(t *testing.T) {
 
 func TestMultipleRetriesShouldNotLooseHeaders(t *testing.T) {
 	attempt := 0
-	expectedHeaderName := "X-Foo-Test-2"
 	expectedHeaderValue := "bar"
 
 	next := http.HandlerFunc(func(rw http.ResponseWriter, req *http.Request) {
@@ -180,44 +179,55 @@ func TestMultipleRetriesShouldNotLooseHeaders(t *testing.T) {
 			return
 		}
 
-		// Request has been successfully written to backend
+		// Request has been successfully written to backend.
 		trace := httptrace.ContextClientTrace(req.Context())
 		trace.WroteHeaders()
 
-		// And we decide to answer to client
+		// And we decide to answer to client.
 		rw.WriteHeader(http.StatusNoContent)
 	})
 
 	retry, err := New(context.Background(), next, dynamic.Retry{Attempts: 3}, &countingRetryListener{}, "traefikTest")
 	require.NoError(t, err)
 
-	responseRecorder := httptest.NewRecorder()
-	retry.ServeHTTP(responseRecorder, testhelpers.MustNewRequest(http.MethodGet, "http://test", http.NoBody))
+	res := httptest.NewRecorder()
+	retry.ServeHTTP(res, testhelpers.MustNewRequest(http.MethodGet, "http://test", http.NoBody))
 
-	headerValue := responseRecorder.Header().Get(expectedHeaderName)
-
-	// Validate if we have the correct header
-	if headerValue != expectedHeaderValue {
-		t.Errorf("Expected to have %s for header %s, got %s", expectedHeaderValue, expectedHeaderName, headerValue)
-	}
+	// The third header attempt is kept.
+	headerValue := res.Header().Get("X-Foo-Test-2")
+	assert.Equal(t, expectedHeaderValue, headerValue)
 
 	// Validate that we don't have headers from previous attempts
 	for i := range attempt {
 		headerName := fmt.Sprintf("X-Foo-Test-%d", i)
-		headerValue = responseRecorder.Header().Get("headerName")
+		headerValue = res.Header().Get(headerName)
 		if headerValue != "" {
 			t.Errorf("Expected no value for header %s, got %s", headerName, headerValue)
 		}
 	}
 }
 
-// countingRetryListener is a Listener implementation to count the times the Retried fn is called.
-type countingRetryListener struct {
-	timesCalled int
-}
+func TestRetryShouldNotLooseHeadersOnWrite(t *testing.T) {
+	next := http.HandlerFunc(func(rw http.ResponseWriter, req *http.Request) {
+		rw.Header().Add("X-Foo-Test", "bar")
 
-func (l *countingRetryListener) Retried(req *http.Request, attempt int) {
-	l.timesCalled++
+		// Request has been successfully written to backend.
+		trace := httptrace.ContextClientTrace(req.Context())
+		trace.WroteHeaders()
+
+		// And we decide to answer to client without calling WriteHeader.
+		_, err := rw.Write([]byte("bar"))
+		require.NoError(t, err)
+	})
+
+	retry, err := New(context.Background(), next, dynamic.Retry{Attempts: 3}, &countingRetryListener{}, "traefikTest")
+	require.NoError(t, err)
+
+	res := httptest.NewRecorder()
+	retry.ServeHTTP(res, testhelpers.MustNewRequest(http.MethodGet, "http://test", http.NoBody))
+
+	headerValue := res.Header().Get("X-Foo-Test")
+	assert.Equal(t, "bar", headerValue)
 }
 
 func TestRetryWithFlush(t *testing.T) {
@@ -387,3 +397,12 @@ func Test1xxResponses(t *testing.T) {
 
 	assert.Equal(t, 0, retryListener.timesCalled)
 }
+
+// countingRetryListener is a Listener implementation to count the times the Retried fn is called.
+type countingRetryListener struct {
+	timesCalled int
+}
+
+func (l *countingRetryListener) Retried(req *http.Request, attempt int) {
+	l.timesCalled++
+}