diff --git a/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/ServerProperties.java b/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/ServerProperties.java
index 7fdab453c71..6d034d04ce5 100644
--- a/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/ServerProperties.java
+++ b/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/ServerProperties.java
@@ -139,7 +139,14 @@ public class ServerProperties implements EmbeddedServletContainerCustomizer, Ord
 	}
 
 	public void setContextPath(String contextPath) {
-		this.contextPath = contextPath;
+		this.contextPath = cleanContextPath(contextPath);
+	}
+
+	private String cleanContextPath(String contextPath) {
+		if (StringUtils.hasText(contextPath) && contextPath.endsWith("/")) {
+			return contextPath.substring(0, contextPath.length() - 1);
+		}
+		return contextPath;
 	}
 
 	public String getDisplayName() {
diff --git a/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesTests.java b/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesTests.java
index c34ac51b3b9..bab6847c868 100644
--- a/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesTests.java
+++ b/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesTests.java
@@ -41,6 +41,7 @@ import org.springframework.boot.context.embedded.ConfigurableEmbeddedServletCont
 import org.springframework.boot.context.embedded.ServletContextInitializer;
 import org.springframework.boot.context.embedded.tomcat.TomcatEmbeddedServletContainerFactory;
 
+import static org.hamcrest.Matchers.equalTo;
 import static org.hamcrest.core.IsInstanceOf.instanceOf;
 import static org.junit.Assert.assertEquals;
 import static org.junit.Assert.assertFalse;
@@ -123,6 +124,20 @@ public class ServerPropertiesTests {
 				.getInternalProxies());
 	}
 
+	@Test
+	public void testTrailingSlashOfContextPathIsRemoved() {
+		new RelaxedDataBinder(this.properties, "server").bind(new MutablePropertyValues(
+				Collections.singletonMap("server.contextPath", "/foo/")));
+		assertThat(this.properties.getContextPath(), equalTo("/foo"));
+	}
+
+	@Test
+	public void testSlashOfContextPathIsDefaultValue() {
+		new RelaxedDataBinder(this.properties, "server").bind(new MutablePropertyValues(
+				Collections.singletonMap("server.contextPath", "/")));
+		assertThat(this.properties.getContextPath(), equalTo(""));
+	}
+
 	@Test
 	public void testCustomizeTomcat() throws Exception {
 		ConfigurableEmbeddedServletContainer factory = mock(ConfigurableEmbeddedServletContainer.class);