diff --git a/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/ServerProperties.java b/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/ServerProperties.java
index 86d9814c75..38bfdf617a 100644
--- a/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/ServerProperties.java
+++ b/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/ServerProperties.java
@@ -231,10 +231,11 @@ public class ServerProperties {
 		}
 
 		private String cleanContextPath(String contextPath) {
-			if (StringUtils.hasText(contextPath) && contextPath.endsWith("/")) {
-				return contextPath.substring(0, contextPath.length() - 1);
+			String candidate = StringUtils.trimWhitespace(contextPath);
+			if (StringUtils.hasText(candidate) && candidate.endsWith("/")) {
+				return candidate.substring(0, candidate.length() - 1);
 			}
-			return contextPath;
+			return candidate;
 		}
 
 		public String getApplicationDisplayName() {
diff --git a/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesTests.java b/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesTests.java
index d09db2f56e..28b373677e 100644
--- a/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesTests.java
+++ b/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesTests.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2018 the original author or authors.
+ * Copyright 2012-2019 the original author or authors.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -149,6 +149,32 @@ public class ServerPropertiesTests {
 		assertThat(this.properties.getServlet().getContextPath()).isEqualTo("");
 	}
 
+	@Test
+	public void testContextPathWithLeadingWhitespace() {
+		bind("server.servlet.context-path", " /assets");
+		assertThat(this.properties.getServlet().getContextPath()).isEqualTo("/assets");
+	}
+
+	@Test
+	public void testContextPathWithTrailingWhitespace() {
+		bind("server.servlet.context-path", "/assets/copy/ ");
+		assertThat(this.properties.getServlet().getContextPath())
+				.isEqualTo("/assets/copy");
+	}
+
+	@Test
+	public void testContextPathWithLeadingAndTrailingWhitespace() {
+		bind("server.servlet.context-path", " /assets ");
+		assertThat(this.properties.getServlet().getContextPath()).isEqualTo("/assets");
+	}
+
+	@Test
+	public void testContextPathWithLeadingAndTrailingWhitespaceAndContextWithSpace() {
+		bind("server.servlet.context-path", "  /assets /copy/    ");
+		assertThat(this.properties.getServlet().getContextPath())
+				.isEqualTo("/assets /copy");
+	}
+
 	@Test
 	public void testCustomizeUriEncoding() {
 		bind("server.tomcat.uri-encoding", "US-ASCII");