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..a27cd7d248 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
@@ -231,8 +231,14 @@ public class ServerProperties {
 		}
 
 		private String cleanContextPath(String contextPath) {
-			if (StringUtils.hasText(contextPath) && contextPath.endsWith("/")) {
-				return contextPath.substring(0, contextPath.length() - 1);
+			if (StringUtils.hasLength(contextPath)) {
+				// remove leading and trailing whitespaces if any exists
+				String ctxPath = StringUtils.trimWhitespace(contextPath);
+
+				if (ctxPath.endsWith("/")) {
+					ctxPath = ctxPath.substring(0, ctxPath.length() - 1);
+				}
+				return ctxPath;
 			}
 			return contextPath;
 		}
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..4b7f561c3b 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
@@ -149,6 +149,32 @@ public class ServerPropertiesTests {
 		assertThat(this.properties.getServlet().getContextPath()).isEqualTo("");
 	}
 
+	@Test
+	public void makeSureTrailingAndLeadingWhitespacesRemoved_case1() {
+		bind("server.servlet.context-path", " /assets");
+		assertThat(this.properties.getServlet().getContextPath()).isEqualTo("/assets");
+	}
+
+	@Test
+	public void makeSureTrailingAndLeadingWhitespacesRemoved_case2() {
+		bind("server.servlet.context-path", " /assets ");
+		assertThat(this.properties.getServlet().getContextPath()).isEqualTo("/assets");
+	}
+
+	@Test
+	public void makeSureTrailingAndLeadingWhitespacesRemoved_case3() {
+		bind("server.servlet.context-path", "/assets/copy/ ");
+		assertThat(this.properties.getServlet().getContextPath())
+				.isEqualTo("/assets/copy");
+	}
+
+	@Test
+	public void makeSureTrailingAndLeadingWhitespacesRemoved_case4() {
+		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");