diff --git a/github/transport.go b/github/transport.go
index d397b02503..b0ee83a915 100644
--- a/github/transport.go
+++ b/github/transport.go
@@ -283,7 +283,9 @@ func (t *RetryTransport) RoundTrip(req *http.Request) (*http.Response, error) {
 			return resp, err
 		}
 
-		time.Sleep(t.retryDelay)
+		if retry < t.maxRetries {
+			sleep(req.Context(), t.retryDelay)
+		}
 	}
 
 	return resp, err
diff --git a/github/transport_test.go b/github/transport_test.go
index eb2b07ba28..442dadee53 100644
--- a/github/transport_test.go
+++ b/github/transport_test.go
@@ -502,6 +502,71 @@ func TestRetryTransport_retry_post_success(t *testing.T) {
 	}
 }
 
+func TestRetryTransport_cancelled(t *testing.T) {
+	ts := githubApiMock([]*mockResponse{
+		{
+			ExpectedUri: "/repos/test/blah",
+			ResponseBody: `{
+  "message": "internal server error"
+}`,
+			StatusCode: 500,
+		},
+	})
+	defer ts.Close()
+	httpClient := http.DefaultClient
+	httpClient.Transport = NewRetryTransport(http.DefaultTransport,
+		WithMaxRetries(1),
+		WithRetryDelay(10*time.Second),
+	)
+	client := github.NewClient(httpClient)
+	u, _ := url.Parse(ts.URL + "/")
+	client.BaseURL = u
+	ctx, cancel := context.WithTimeout(context.Background(), 100*time.Millisecond)
+	defer cancel()
+	start := time.Now()
+	_, _, err := client.Repositories.Get(ctx, "test", "blah")
+	if !errors.Is(err, context.DeadlineExceeded) {
+		t.Fatalf("Expected context.DeadlineExceeded, got: %v", err)
+	}
+	if time.Since(start) > time.Second {
+		t.Fatalf("Waited longer than expected: %s", time.Since(start))
+	}
+}
+
+func TestRetryTransport_no_sleep_after_last_retry(t *testing.T) {
+	ts := githubApiMock([]*mockResponse{
+		{
+			ExpectedUri: "/repos/test/blah",
+			ResponseBody: `{
+  "message": "internal server error"
+}`,
+			StatusCode: 500,
+		},
+		{
+			ExpectedUri: "/repos/test/blah",
+			ResponseBody: `{
+  "message": "internal server error"
+}`,
+			StatusCode: 500,
+		},
+	})
+	defer ts.Close()
+	httpClient := http.DefaultClient
+	httpClient.Transport = NewRetryTransport(http.DefaultTransport,
+		WithMaxRetries(1),
+		WithRetryDelay(10*time.Second),
+	)
+	client := github.NewClient(httpClient)
+	u, _ := url.Parse(ts.URL + "/")
+	client.BaseURL = u
+	start := time.Now()
+	ctx := context.WithValue(context.Background(), ctxId, t.Name())
+	_, _, _ = client.Repositories.Get(ctx, "test", "blah")
+	if time.Since(start) > time.Second {
+		t.Fatalf("Slept after last retry: %s", time.Since(start))
+	}
+}
+
 type mockResponse struct {
 	ExpectedUri     string
 	ExpectedMethod  string