diff --git a/source/common/router/router.cc b/source/common/router/router.cc
index cd461bacb7ca0..27d670149f0bf 100644
--- a/source/common/router/router.cc
+++ b/source/common/router/router.cc
@@ -652,9 +652,6 @@ Http::FilterHeadersStatus Filter::decodeHeaders(Http::RequestHeaderMap& headers,
   }
   callbacks_->streamInfo().setAttemptCount(attempt_count_);
 
-  // Inject the active span's tracing context into the request headers.
-  callbacks_->activeSpan().injectContext(headers);
-
   route_entry_->finalizeRequestHeaders(headers, callbacks_->streamInfo(),
                                        !config_.suppress_envoy_headers_);
   FilterUtility::setUpstreamScheme(
diff --git a/source/common/router/upstream_request.cc b/source/common/router/upstream_request.cc
index 25f763e17e7c0..c336eaffaf46c 100644
--- a/source/common/router/upstream_request.cc
+++ b/source/common/router/upstream_request.cc
@@ -486,6 +486,11 @@ void UpstreamRequest::onPoolReady(
 
   if (span_ != nullptr) {
     span_->injectContext(*parent_.downstreamHeaders());
+  } else {
+    // No independent child span for current upstream request then inject the parent span's tracing
+    // context into the request headers.
+    // The injectContext() of the parent span may be called repeatedly when the request is retried.
+    parent_.callbacks()->activeSpan().injectContext(*parent_.downstreamHeaders());
   }
 
   upstreamTiming().onFirstUpstreamTxByteSent(parent_.callbacks()->dispatcher().timeSource());
diff --git a/test/common/router/router_2_test.cc b/test/common/router/router_2_test.cc
index 2f1f3c50bd061..a6a096d45b446 100644
--- a/test/common/router/router_2_test.cc
+++ b/test/common/router/router_2_test.cc
@@ -532,6 +532,43 @@ TEST_F(RouterTestChildSpan, ResetRetryFlow) {
   response_decoder->decodeHeaders(std::move(response_headers), true);
 }
 
+class RouterTestNoChildSpan : public RouterTestBase {
+public:
+  RouterTestNoChildSpan()
+      : RouterTestBase(false, false, false, Protobuf::RepeatedPtrField<std::string>{}) {}
+};
+
+TEST_F(RouterTestNoChildSpan, BasicFlow) {
+  EXPECT_CALL(callbacks_.route_->route_entry_, timeout())
+      .WillOnce(Return(std::chrono::milliseconds(0)));
+  EXPECT_CALL(callbacks_.dispatcher_, createTimer_(_)).Times(0);
+
+  NiceMock<Http::MockRequestEncoder> encoder;
+  Http::ResponseDecoder* response_decoder = nullptr;
+  EXPECT_CALL(cm_.thread_local_cluster_.conn_pool_, newStream(_, _, _))
+      .WillOnce(
+          Invoke([&](Http::ResponseDecoder& decoder, Http::ConnectionPool::Callbacks& callbacks,
+                     const Http::ConnectionPool::Instance::StreamOptions&)
+                     -> Http::ConnectionPool::Cancellable* {
+            response_decoder = &decoder;
+            EXPECT_CALL(callbacks_.active_span_, injectContext(_));
+            callbacks.onPoolReady(encoder, cm_.thread_local_cluster_.conn_pool_.host_,
+                                  upstream_stream_info_, Http::Protocol::Http10);
+            return nullptr;
+          }));
+
+  Http::TestRequestHeaderMapImpl headers;
+  HttpTestUtility::addDefaultHeaders(headers);
+  router_.decodeHeaders(headers, true);
+  EXPECT_EQ(1U,
+            callbacks_.route_->route_entry_.virtual_cluster_.stats().upstream_rq_total_.value());
+
+  Http::ResponseHeaderMapPtr response_headers(
+      new Http::TestResponseHeaderMapImpl{{":status", "200"}});
+  ASSERT(response_decoder);
+  response_decoder->decodeHeaders(std::move(response_headers), true);
+}
+
 namespace {
 
 Protobuf::RepeatedPtrField<std::string> protobufStrList(const std::vector<std::string>& v) {
diff --git a/test/common/router/router_test.cc b/test/common/router/router_test.cc
index 24fee216cae12..178c12db1f5e4 100644
--- a/test/common/router/router_test.cc
+++ b/test/common/router/router_test.cc
@@ -412,7 +412,6 @@ TEST_F(RouterTest, Http1Upstream) {
   Http::TestRequestHeaderMapImpl headers;
   HttpTestUtility::addDefaultHeaders(headers);
   EXPECT_CALL(callbacks_.route_->route_entry_, finalizeRequestHeaders(_, _, true));
-  EXPECT_CALL(span_, injectContext(_));
   router_.decodeHeaders(headers, true);
   EXPECT_EQ("10", headers.get_("x-envoy-expected-rq-timeout-ms"));
 
@@ -432,7 +431,6 @@ TEST_F(RouterTest, Http2Upstream) {
 
   Http::TestRequestHeaderMapImpl headers;
   HttpTestUtility::addDefaultHeaders(headers);
-  EXPECT_CALL(span_, injectContext(_));
   router_.decodeHeaders(headers, true);
 
   // When the router filter gets reset we should cancel the pool request.
@@ -739,7 +737,6 @@ TEST_F(RouterTest, MaintenanceMode) {
   EXPECT_CALL(callbacks_, encodeHeaders_(HeaderMapEqualRef(&response_headers), false));
   EXPECT_CALL(callbacks_, encodeData(_, true));
   EXPECT_CALL(callbacks_.stream_info_, setResponseFlag(StreamInfo::ResponseFlag::UpstreamOverflow));
-  EXPECT_CALL(span_, injectContext(_)).Times(0);
 
   Http::TestRequestHeaderMapImpl headers;
   HttpTestUtility::addDefaultHeaders(headers);
@@ -4556,7 +4553,6 @@ TEST_F(RouterTest, DirectResponse) {
 
   Http::TestResponseHeaderMapImpl response_headers{{":status", "200"}};
   EXPECT_CALL(callbacks_, encodeHeaders_(HeaderMapEqualRef(&response_headers), true));
-  EXPECT_CALL(span_, injectContext(_)).Times(0);
   Http::TestRequestHeaderMapImpl headers;
   HttpTestUtility::addDefaultHeaders(headers);
   router_.decodeHeaders(headers, true);
@@ -4606,7 +4602,6 @@ TEST_F(RouterTest, DirectResponseWithLocation) {
   Http::TestResponseHeaderMapImpl response_headers{{":status", "201"},
                                                    {"location", "http://host/"}};
   EXPECT_CALL(callbacks_, encodeHeaders_(HeaderMapEqualRef(&response_headers), true));
-  EXPECT_CALL(span_, injectContext(_)).Times(0);
   Http::TestRequestHeaderMapImpl headers;
   HttpTestUtility::addDefaultHeaders(headers);
   router_.decodeHeaders(headers, true);
@@ -4630,7 +4625,6 @@ TEST_F(RouterTest, DirectResponseWithoutLocation) {
 
   Http::TestResponseHeaderMapImpl response_headers{{":status", "200"}};
   EXPECT_CALL(callbacks_, encodeHeaders_(HeaderMapEqualRef(&response_headers), true));
-  EXPECT_CALL(span_, injectContext(_)).Times(0);
   Http::TestRequestHeaderMapImpl headers;
   HttpTestUtility::addDefaultHeaders(headers);
   router_.decodeHeaders(headers, true);
@@ -5653,7 +5647,6 @@ TEST_F(RouterTest, ApplicationProtocols) {
 
   Http::TestRequestHeaderMapImpl headers;
   HttpTestUtility::addDefaultHeaders(headers);
-  EXPECT_CALL(span_, injectContext(_));
   router_.decodeHeaders(headers, true);
 
   // When the router filter gets reset we should cancel the pool request.