diff --git a/web/src/main/java/org/apache/shiro/web/filter/PathMatchingFilter.java b/web/src/main/java/org/apache/shiro/web/filter/PathMatchingFilter.java
index e507ad32d4..be1da71a54 100644
--- a/web/src/main/java/org/apache/shiro/web/filter/PathMatchingFilter.java
+++ b/web/src/main/java/org/apache/shiro/web/filter/PathMatchingFilter.java
@@ -123,10 +123,12 @@ protected String getPathWithinApplication(ServletRequest request) {
      */
     protected boolean pathsMatch(String path, ServletRequest request) {
         String requestURI = getPathWithinApplication(request);
-        if (requestURI != null && requestURI.endsWith(DEFAULT_PATH_SEPARATOR)) {
+        if (requestURI != null && !DEFAULT_PATH_SEPARATOR.equals(requestURI)
+                && requestURI.endsWith(DEFAULT_PATH_SEPARATOR)) {
             requestURI = requestURI.substring(0, requestURI.length() - 1);
         }
-        if (path != null && path.endsWith(DEFAULT_PATH_SEPARATOR)) {
+        if (path != null && !DEFAULT_PATH_SEPARATOR.equals(path)
+                && path.endsWith(DEFAULT_PATH_SEPARATOR)) {
             path = path.substring(0, path.length() - 1);
         }
         log.trace("Attempting to match pattern '{}' with current requestURI '{}'...", path, Encode.forHtml(requestURI));
diff --git a/web/src/main/java/org/apache/shiro/web/filter/mgt/PathMatchingFilterChainResolver.java b/web/src/main/java/org/apache/shiro/web/filter/mgt/PathMatchingFilterChainResolver.java
index 7adcda733f..c35ab9b290 100644
--- a/web/src/main/java/org/apache/shiro/web/filter/mgt/PathMatchingFilterChainResolver.java
+++ b/web/src/main/java/org/apache/shiro/web/filter/mgt/PathMatchingFilterChainResolver.java
@@ -105,7 +105,8 @@ public FilterChain getChain(ServletRequest request, ServletResponse response, Fi
         // in spring web, the requestURI "/resource/menus" ---- "resource/menus/" bose can access the resource
         // but the pathPattern match "/resource/menus" can not match "resource/menus/"
         // user can use requestURI + "/" to simply bypassed chain filter, to bypassed shiro protect
-        if(requestURI != null && requestURI.endsWith(DEFAULT_PATH_SEPARATOR)) {
+        if(requestURI != null && !DEFAULT_PATH_SEPARATOR.equals(requestURI)
+                && requestURI.endsWith(DEFAULT_PATH_SEPARATOR)) {
             requestURI = requestURI.substring(0, requestURI.length() - 1);
         }
 
@@ -113,7 +114,8 @@ public FilterChain getChain(ServletRequest request, ServletResponse response, Fi
         //the 'chain names' in this implementation are actually path patterns defined by the user.  We just use them
         //as the chain name for the FilterChainManager's requirements
         for (String pathPattern : filterChainManager.getChainNames()) {
-            if (pathPattern != null && pathPattern.endsWith(DEFAULT_PATH_SEPARATOR)) {
+            if (pathPattern != null && !DEFAULT_PATH_SEPARATOR.equals(pathPattern)
+                    && pathPattern.endsWith(DEFAULT_PATH_SEPARATOR)) {
                 pathPattern = pathPattern.substring(0, pathPattern.length() - 1);
             }
 
diff --git a/web/src/test/java/org/apache/shiro/web/filter/PathMatchingFilterTest.java b/web/src/test/java/org/apache/shiro/web/filter/PathMatchingFilterTest.java
index 116aaae7d4..c6e81d4139 100644
--- a/web/src/test/java/org/apache/shiro/web/filter/PathMatchingFilterTest.java
+++ b/web/src/test/java/org/apache/shiro/web/filter/PathMatchingFilterTest.java
@@ -121,6 +121,20 @@ public void testEnabled() throws Exception {
         verify(request);
     }
 
+    /**
+     * Test asserting <a href="https://issues.apache.org/jira/browse/SHIRO-742">SHIRO-742<a/>.
+     */
+    @Test
+    public void testPathMatchEqualUrlSeparatorEnabled() {
+        expect(request.getContextPath()).andReturn(CONTEXT_PATH).anyTimes();
+        expect(request.getRequestURI()).andReturn("/").anyTimes();
+        replay(request);
+
+        boolean matchEnabled = filter.pathsMatch("/", request);
+        assertTrue("PathMatch can match URL end with Separator", matchEnabled);
+        verify(request);
+    }
+
     /**
      * Test asserting <a href="https://issues.apache.org/jira/browse/SHIRO-682">SHIRO-682<a/>.
      */
diff --git a/web/src/test/java/org/apache/shiro/web/filter/mgt/PathMatchingFilterChainResolverTest.java b/web/src/test/java/org/apache/shiro/web/filter/mgt/PathMatchingFilterChainResolverTest.java
index 68a8fa2e00..758be4d1f3 100644
--- a/web/src/test/java/org/apache/shiro/web/filter/mgt/PathMatchingFilterChainResolverTest.java
+++ b/web/src/test/java/org/apache/shiro/web/filter/mgt/PathMatchingFilterChainResolverTest.java
@@ -186,6 +186,28 @@ public void testGetChain() {
         verify(request);
     }
 
+    /**
+     * Test asserting <a href="https://issues.apache.org/jira/browse/SHIRO-742">SHIRO-742<a/>.
+     */
+    @Test
+    public void testGetChainEqualUrlSeparator() {
+        HttpServletRequest request = createNiceMock(HttpServletRequest.class);
+        HttpServletResponse response = createNiceMock(HttpServletResponse.class);
+        FilterChain chain = createNiceMock(FilterChain.class);
+
+        //ensure at least one chain is defined:
+        resolver.getFilterChainManager().addToChain("/", "authcBasic");
+
+        expect(request.getAttribute(WebUtils.INCLUDE_CONTEXT_PATH_ATTRIBUTE)).andReturn(null).anyTimes();
+        expect(request.getContextPath()).andReturn("");
+        expect(request.getRequestURI()).andReturn("/");
+        replay(request);
+
+        FilterChain resolved = resolver.getChain(request, response, chain);
+        assertNotNull(resolved);
+        verify(request);
+    }
+
     /**
      * Test asserting <a href="https://issues.apache.org/jira/browse/SHIRO-682">SHIRO-682<a/>.
      */