diff --git a/packages/@vuepress/theme-default/util/index.js b/packages/@vuepress/theme-default/util/index.js
index 92fcd3b311..6ec5b41b2d 100644
--- a/packages/@vuepress/theme-default/util/index.js
+++ b/packages/@vuepress/theme-default/util/index.js
@@ -200,6 +200,7 @@ export function resolveMatchingConfig (regularPath, config) {
       config: config
     }
   }
+
   for (const base in config) {
     if (ensureEndingSlash(regularPath).indexOf(encodeURI(base)) === 0) {
       return {
@@ -217,6 +218,29 @@ function ensureEndingSlash (path) {
     : path + '/'
 }
 
+const baseMap = new Map()
+/**
+ * handle multilevel sidebar base config
+ * @param {*} item
+ * @param {*} base
+ * @param {*} groupDepth
+ * @returns
+ */
+function resolveBase (item, base, groupDepth) {
+  if (groupDepth <= 2) {
+    !baseMap.has(groupDepth.toString()) && baseMap.set(groupDepth.toString(), base)
+    return base
+  }
+
+  if (!baseMap.has(groupDepth.toString())) {
+    const prev = baseMap.get((groupDepth - 1).toString())
+    baseMap.set(groupDepth.toString(), `${prev + item.title}\/`)
+    return baseMap.get(groupDepth.toString())
+  } else {
+    return baseMap.get(groupDepth.toString())
+  }
+}
+
 function resolveItem (item, pages, base, groupDepth = 1) {
   if (typeof item === 'string') {
     return resolvePage(pages, item, base)
@@ -237,7 +261,7 @@ function resolveItem (item, pages, base, groupDepth = 1) {
       title: item.title,
       sidebarDepth: item.sidebarDepth,
       initialOpenGroupIndex: item.initialOpenGroupIndex,
-      children: children.map(child => resolveItem(child, pages, base, groupDepth + 1)),
+      children: children.map(child => resolveItem(child, pages, resolveBase(item, base, groupDepth + 1), groupDepth + 1)),
       collapsable: item.collapsable !== false
     }
   }
diff --git a/packages/@vuepress/types/src/theme-default.ts b/packages/@vuepress/types/src/theme-default.ts
index c086041e2a..bc55cd7446 100644
--- a/packages/@vuepress/types/src/theme-default.ts
+++ b/packages/@vuepress/types/src/theme-default.ts
@@ -84,7 +84,7 @@ export type SidebarItem4Group = {
   /**
    * Sidebar children.
    */
-  children?: Array<SidebarItem4Shortcut>;
+  children?: Array<SidebarItem4Shortcut | SidebarItem4Group>;
 };
 
 /**