diff --git a/lib/ContextModule.js b/lib/ContextModule.js
index e7170d44b53..43b9071d68f 100644
--- a/lib/ContextModule.js
+++ b/lib/ContextModule.js
@@ -61,7 +61,7 @@ const makeSerializable = require("./util/makeSerializable");
 
 /**
  * @typedef {Object} ContextModuleOptionsExtras
- * @property {string} resource
+ * @property {string|string[]} resource
  * @property {string=} resourceQuery
  * @property {string=} resourceFragment
  * @property {TODO} resolveOptions
@@ -92,23 +92,34 @@ class ContextModule extends Module {
 	 * @param {ContextModuleOptions} options options object
 	 */
 	constructor(resolveDependencies, options) {
-		const parsed = parseResource(options ? options.resource : "");
-		const resource = parsed.path;
-		const resourceQuery = (options && options.resourceQuery) || parsed.query;
-		const resourceFragment =
-			(options && options.resourceFragment) || parsed.fragment;
-
-		super("javascript/dynamic", resource);
+		if (typeof options.resource !== "string") {
+			super("javascript/dynamic");
+			/** @type {ContextModuleOptions} */
+			this.options = {
+				...options,
+				resource: options.resource,
+				resourceQuery: options.resourceQuery || "",
+				resourceFragment: options.resourceFragment || ""
+			};
+		} else {
+			const parsed = parseResource(options.resource);
+			const resource = parsed.path;
+			const resourceQuery = (options && options.resourceQuery) || parsed.query;
+			const resourceFragment =
+				(options && options.resourceFragment) || parsed.fragment;
+
+			super("javascript/dynamic", resource);
+			/** @type {ContextModuleOptions} */
+			this.options = {
+				...options,
+				resource,
+				resourceQuery,
+				resourceFragment
+			};
+		}
 
 		// Info from Factory
 		this.resolveDependencies = resolveDependencies;
-		/** @type {ContextModuleOptions} */
-		this.options = {
-			...options,
-			resource,
-			resourceQuery,
-			resourceFragment
-		};
 		if (options && options.resolveOptions !== undefined) {
 			this.resolveOptions = options.resolveOptions;
 		}
@@ -155,7 +166,11 @@ class ContextModule extends Module {
 	}
 
 	_createIdentifier() {
-		let identifier = this.context;
+		let identifier =
+			this.context ||
+			(typeof this.options.resource === "string"
+				? this.options.resource
+				: this.options.resource.join("|"));
 		if (this.options.resourceQuery) {
 			identifier += `|${this.options.resourceQuery}`;
 		}
@@ -220,7 +235,16 @@ class ContextModule extends Module {
 	 * @returns {string} a user readable identifier of the module
 	 */
 	readableIdentifier(requestShortener) {
-		let identifier = requestShortener.shorten(this.context) + "/";
+		let identifier;
+		if (this.context) {
+			identifier = requestShortener.shorten(this.context) + "/";
+		} else if (typeof this.options.resource === "string") {
+			identifier = requestShortener.shorten(this.options.resource) + "/";
+		} else {
+			identifier =
+				this.options.resource.map(r => requestShortener.shorten(r)).join("/") +
+				"/";
+		}
 		if (this.options.resourceQuery) {
 			identifier += ` ${this.options.resourceQuery}`;
 		}
@@ -270,11 +294,30 @@ class ContextModule extends Module {
 	 * @returns {string | null} an identifier for library inclusion
 	 */
 	libIdent(options) {
-		let identifier = contextify(
-			options.context,
-			this.context,
-			options.associatedObjectForCache
-		);
+		let identifier;
+
+		if (this.context) {
+			identifier = contextify(
+				options.context,
+				this.context,
+				options.associatedObjectForCache
+			);
+		} else if (typeof this.options.resource === "string") {
+			identifier = contextify(
+				options.context,
+				this.options.resource,
+				options.associatedObjectForCache
+			);
+		} else {
+			const arr = [];
+			for (const res of this.options.resource) {
+				arr.push(
+					contextify(options.context, res, options.associatedObjectForCache)
+				);
+			}
+			identifier = arr.join("|");
+		}
+
 		if (this.layer) identifier = `(${this.layer})/${identifier}`;
 		if (this.options.mode) {
 			identifier += ` ${this.options.mode}`;
@@ -442,7 +485,11 @@ class ContextModule extends Module {
 			compilation.fileSystemInfo.createSnapshot(
 				startTime,
 				null,
-				[this.context],
+				this.context
+					? [this.context]
+					: typeof this.options.resource === "string"
+					? [this.options.resource]
+					: this.options.resource,
 				null,
 				SNAPSHOT_OPTIONS,
 				(err, snapshot) => {
@@ -466,7 +513,13 @@ class ContextModule extends Module {
 		missingDependencies,
 		buildDependencies
 	) {
-		contextDependencies.add(this.context);
+		if (this.context) {
+			contextDependencies.add(this.context);
+		} else if (typeof this.options.resource === "string") {
+			contextDependencies.add(this.options.resource);
+		} else {
+			for (const res of this.options.resource) contextDependencies.add(res);
+		}
 	}
 
 	/**
diff --git a/lib/ContextModuleFactory.js b/lib/ContextModuleFactory.js
index f667e11f87f..27bd39c7445 100644
--- a/lib/ContextModuleFactory.js
+++ b/lib/ContextModuleFactory.js
@@ -167,6 +167,9 @@ module.exports = class ContextModuleFactory extends ModuleFactory {
 				asyncLib.parallel(
 					[
 						callback => {
+							const results = [];
+							const yield_ = obj => results.push(obj);
+
 							contextResolver.resolve(
 								{},
 								context,
@@ -174,11 +177,12 @@ module.exports = class ContextModuleFactory extends ModuleFactory {
 								{
 									fileDependencies,
 									missingDependencies,
-									contextDependencies
+									contextDependencies,
+									yield: yield_
 								},
-								(err, result) => {
+								err => {
 									if (err) return callback(err);
-									callback(null, result);
+									callback(null, results);
 								}
 							);
 						},
@@ -213,14 +217,17 @@ module.exports = class ContextModuleFactory extends ModuleFactory {
 								contextDependencies
 							});
 						}
-
+						const [contextResult, loaderResult] = result;
 						this.hooks.afterResolve.callAsync(
 							{
 								addon:
 									loadersPrefix +
-									result[1].join("!") +
-									(result[1].length > 0 ? "!" : ""),
-								resource: result[0],
+									loaderResult.join("!") +
+									(loaderResult.length > 0 ? "!" : ""),
+								resource:
+									contextResult.length > 1
+										? contextResult.map(r => r.path)
+										: contextResult[0].path,
 								resolveDependencies: this.resolveDependencies.bind(this),
 								...beforeResolveResult
 							},
@@ -278,26 +285,28 @@ module.exports = class ContextModuleFactory extends ModuleFactory {
 		} = options;
 		if (!regExp || !resource) return callback(null, []);
 
-		const addDirectoryChecked = (directory, visited, callback) => {
+		let severalContexts = false;
+		const addDirectoryChecked = (ctx, directory, visited, callback) => {
 			fs.realpath(directory, (err, realPath) => {
 				if (err) return callback(err);
 				if (visited.has(realPath)) return callback(null, []);
 				let recursionStack;
 				addDirectory(
+					ctx,
 					directory,
 					(dir, callback) => {
 						if (recursionStack === undefined) {
 							recursionStack = new Set(visited);
 							recursionStack.add(realPath);
 						}
-						addDirectoryChecked(dir, recursionStack, callback);
+						addDirectoryChecked(ctx, dir, recursionStack, callback);
 					},
 					callback
 				);
 			});
 		};
 
-		const addDirectory = (directory, addSubDirectory, callback) => {
+		const addDirectory = (ctx, directory, addSubDirectory, callback) => {
 			fs.readdir(directory, (err, files) => {
 				if (err) return callback(err);
 				const processedFiles = cmf.hooks.contextModuleFiles.call(
@@ -330,10 +339,9 @@ module.exports = class ContextModuleFactory extends ModuleFactory {
 									(!include || subResource.match(include))
 								) {
 									const obj = {
-										context: resource,
+										context: ctx,
 										request:
-											"." +
-											subResource.substr(resource.length).replace(/\\/g, "/")
+											"." + subResource.substr(ctx.length).replace(/\\/g, "/")
 									};
 
 									this.hooks.alternativeRequests.callAsync(
@@ -344,8 +352,11 @@ module.exports = class ContextModuleFactory extends ModuleFactory {
 											alternatives = alternatives
 												.filter(obj => regExp.test(obj.request))
 												.map(obj => {
+													const request = severalContexts
+														? join(fs, obj.context, obj.request)
+														: obj.request;
 													const dep = new ContextElementDependency(
-														obj.request + resourceQuery + resourceFragment,
+														request + resourceQuery + resourceFragment,
 														obj.request,
 														typePrefix,
 														category,
@@ -382,12 +393,38 @@ module.exports = class ContextModuleFactory extends ModuleFactory {
 			});
 		};
 
-		if (typeof fs.realpath === "function") {
-			addDirectoryChecked(resource, new Set(), callback);
+		const addSubDirectory = (ctx, dir, callback) =>
+			addDirectory(ctx, dir, addSubDirectory, callback);
+
+		const visitResource = (resource, callback) => {
+			if (typeof fs.realpath === "function") {
+				addDirectoryChecked(resource, new Set(), callback);
+			} else {
+				addDirectory(resource, resource, addSubDirectory, callback);
+			}
+		};
+
+		if (typeof resource === "string") {
+			visitResource(resource, callback);
 		} else {
-			const addSubDirectory = (dir, callback) =>
-				addDirectory(dir, addSubDirectory, callback);
-			addDirectory(resource, addSubDirectory, callback);
+			severalContexts = true;
+			asyncLib.map(resource, visitResource, (err, result) => {
+				if (err) return callback(err);
+
+				// result dependencies should have unique userRequest
+				// ordered by resolve result
+				const temp = new Set();
+				const res = [];
+				for (let i = 0; i < result.length; i++) {
+					const inner = result[i];
+					for (const el of inner) {
+						if (temp.has(el.userRequest)) continue;
+						res.push(el);
+						temp.add(el.userRequest);
+					}
+				}
+				callback(null, res);
+			});
 		}
 	}
 };
diff --git a/package.json b/package.json
index e76e0cd4938..08abd640526 100644
--- a/package.json
+++ b/package.json
@@ -14,7 +14,7 @@
     "acorn-import-assertions": "^1.7.6",
     "browserslist": "^4.14.5",
     "chrome-trace-event": "^1.0.2",
-    "enhanced-resolve": "^5.8.3",
+    "enhanced-resolve": "^5.9.0",
     "es-module-lexer": "^0.9.0",
     "eslint-scope": "5.1.1",
     "events": "^3.2.0",
diff --git a/test/configCases/resolve/issue-11335-context-module/index.js b/test/configCases/resolve/issue-11335-context-module/index.js
new file mode 100644
index 00000000000..d4784570ea4
--- /dev/null
+++ b/test/configCases/resolve/issue-11335-context-module/index.js
@@ -0,0 +1,18 @@
+import a from "app/widgets/a";
+import b from "app/widgets/b";
+import c from "app/widgets/c";
+
+
+it("static imports order", () => {
+	expect(a).toBe("main/widgets/a");
+	expect(b).toBe("main/widgets/b");
+	expect(c).toBe("foo/widgets/c");
+});
+
+const load = id => import(/* webpackMode: "eager" */ `app/widgets/${id}?query#hash`);
+
+it("dynamic imports order", async () => {
+	expect((await load("a")).default).toBe("main/widgets/a");
+	expect((await load("b")).default).toBe("main/widgets/b");
+	expect((await load("c")).default).toBe("foo/widgets/c");
+});
diff --git a/test/configCases/resolve/issue-11335-context-module/src/foo/widgets/b.js b/test/configCases/resolve/issue-11335-context-module/src/foo/widgets/b.js
new file mode 100644
index 00000000000..9b6f2974934
--- /dev/null
+++ b/test/configCases/resolve/issue-11335-context-module/src/foo/widgets/b.js
@@ -0,0 +1 @@
+export default "foo/widgets/b";
diff --git a/test/configCases/resolve/issue-11335-context-module/src/foo/widgets/c.js b/test/configCases/resolve/issue-11335-context-module/src/foo/widgets/c.js
new file mode 100644
index 00000000000..0de4d4fb702
--- /dev/null
+++ b/test/configCases/resolve/issue-11335-context-module/src/foo/widgets/c.js
@@ -0,0 +1 @@
+export default "foo/widgets/c";
diff --git a/test/configCases/resolve/issue-11335-context-module/src/main/widgets/a.js b/test/configCases/resolve/issue-11335-context-module/src/main/widgets/a.js
new file mode 100644
index 00000000000..b6d0dbb4492
--- /dev/null
+++ b/test/configCases/resolve/issue-11335-context-module/src/main/widgets/a.js
@@ -0,0 +1 @@
+export default "main/widgets/a";
diff --git a/test/configCases/resolve/issue-11335-context-module/src/main/widgets/b.js b/test/configCases/resolve/issue-11335-context-module/src/main/widgets/b.js
new file mode 100644
index 00000000000..0b8fa8212af
--- /dev/null
+++ b/test/configCases/resolve/issue-11335-context-module/src/main/widgets/b.js
@@ -0,0 +1 @@
+export default "main/widgets/b";
diff --git a/test/configCases/resolve/issue-11335-context-module/webpack.config.js b/test/configCases/resolve/issue-11335-context-module/webpack.config.js
new file mode 100644
index 00000000000..d1c50dcaac7
--- /dev/null
+++ b/test/configCases/resolve/issue-11335-context-module/webpack.config.js
@@ -0,0 +1,10 @@
+const path = require("path");
+
+/** @type {import("../../../../").Configuration} */
+module.exports = {
+	resolve: {
+		alias: {
+			app: [path.join(__dirname, "src/main"), path.join(__dirname, "src/foo")]
+		}
+	}
+};
diff --git a/types.d.ts b/types.d.ts
index 09e63e8706a..b27474e113e 100644
--- a/types.d.ts
+++ b/types.d.ts
@@ -2519,7 +2519,7 @@ declare interface ContextModuleOptions {
 	 * exports referenced from modules (won't be mangled)
 	 */
 	referencedExports?: string[][];
-	resource: string;
+	resource: string | string[];
 	resourceQuery?: string;
 	resourceFragment?: string;
 	resolveOptions: any;
@@ -9389,6 +9389,11 @@ declare interface ResolveContext {
 	 * log function
 	 */
 	log?: (arg0: string) => void;
+
+	/**
+	 * yield result, if provided plugins can return several results
+	 */
+	yield?: (arg0: ResolveRequest) => void;
 }
 declare interface ResolveData {
 	contextInfo: ModuleFactoryCreateDataContextInfo;
@@ -11835,7 +11840,7 @@ declare interface UserResolveOptions {
 	restrictions?: (string | RegExp)[];
 
 	/**
-	 * Use only the sync constiants of the file system calls
+	 * Use only the sync constraints of the file system calls
 	 */
 	useSyncFileSystemCalls?: boolean;
 
diff --git a/yarn.lock b/yarn.lock
index 8a36e5ff05d..925c133ad25 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -2256,10 +2256,10 @@ enhanced-resolve@^4.0.0:
     memory-fs "^0.5.0"
     tapable "^1.0.0"
 
-enhanced-resolve@^5.8.3:
-  version "5.8.3"
-  resolved "https://registry.yarnpkg.com/enhanced-resolve/-/enhanced-resolve-5.8.3.tgz#6d552d465cce0423f5b3d718511ea53826a7b2f0"
-  integrity sha512-EGAbGvH7j7Xt2nc0E7D99La1OiEs8LnyimkRgwExpUMScN6O+3x9tIWs7PLQZVNx4YD+00skHXPXi1yQHpAmZA==
+enhanced-resolve@^5.9.0:
+  version "5.9.0"
+  resolved "https://registry.yarnpkg.com/enhanced-resolve/-/enhanced-resolve-5.9.0.tgz#49ac24953ac8452ed8fed2ef1340fc8e043667ee"
+  integrity sha512-weDYmzbBygL7HzGGS26M3hGQx68vehdEg6VUmqSOaFzXExFqlnKuSvsEJCVGQHScS8CQMbrAqftT+AzzHNt/YA==
   dependencies:
     graceful-fs "^4.2.4"
     tapable "^2.2.0"