diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/undertow/UndertowServletWebServer.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/undertow/UndertowServletWebServer.java
index 1497c6c086c..6aaffccf10e 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/undertow/UndertowServletWebServer.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/undertow/UndertowServletWebServer.java
@@ -304,6 +304,7 @@ public class UndertowServletWebServer implements WebServer {
 			this.started = false;
 			try {
 				this.manager.stop();
+				this.manager.undeploy();
 				this.undertow.stop();
 			}
 			catch (Exception ex) {
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/servlet/server/AbstractServletWebServerFactoryTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/servlet/server/AbstractServletWebServerFactoryTests.java
index 8e50f4e14a2..9d0ee14e847 100644
--- a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/servlet/server/AbstractServletWebServerFactoryTests.java
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/servlet/server/AbstractServletWebServerFactoryTests.java
@@ -55,6 +55,8 @@ import javax.servlet.FilterChain;
 import javax.servlet.FilterConfig;
 import javax.servlet.GenericServlet;
 import javax.servlet.ServletContext;
+import javax.servlet.ServletContextEvent;
+import javax.servlet.ServletContextListener;
 import javax.servlet.ServletException;
 import javax.servlet.ServletRequest;
 import javax.servlet.ServletResponse;
@@ -1038,6 +1040,17 @@ public abstract class AbstractServletWebServerFactoryTests {
 		assertThat(servletContext.getSessionCookieConfig().getMaxAge()).isEqualTo(60);
 	}
 
+	@Test
+	public void servletContextListenerContextDestroyedIsCalledWhenContainerIsStopped()
+			throws Exception {
+		ServletContextListener listener = mock(ServletContextListener.class);
+		this.webServer = getFactory()
+				.getWebServer((servletContext) -> servletContext.addListener(listener));
+		this.webServer.start();
+		this.webServer.stop();
+		verify(listener).contextDestroyed(any(ServletContextEvent.class));
+	}
+
 	protected abstract void addConnector(int port,
 			AbstractServletWebServerFactory factory);