diff --git a/packages/playwright-test/src/transform.ts b/packages/playwright-test/src/transform.ts
index 7273fcb178..1d273fc796 100644
--- a/packages/playwright-test/src/transform.ts
+++ b/packages/playwright-test/src/transform.ts
@@ -100,23 +100,52 @@ export function resolveHook(filename: string, specifier: string): string | undef
     return;
   const tsconfig = loadAndValidateTsconfigForFile(filename);
   if (tsconfig) {
+    let longestPrefixLength = -1;
+    let pathMatchedByLongestPrefix: string | undefined;
+
     for (const { key, values } of tsconfig.paths) {
-      const keyHasStar = key[key.length - 1] === '*';
-      const matches = specifier.startsWith(keyHasStar ? key.substring(0, key.length - 1) : key);
-      if (!matches)
-        continue;
+      let matchedPartOfSpecifier = specifier;
+
+      const [keyPrefix, keySuffix] = key.split('*');
+      if (key.includes('*')) {
+        // * If pattern contains '*' then to match pattern "<prefix>*<suffix>" module name must start with the <prefix> and end with <suffix>.
+        // * <MatchedStar> denotes part of the module name between <prefix> and <suffix>.
+        // * If module name can be matches with multiple patterns then pattern with the longest prefix will be picked.
+        // https://github.com/microsoft/TypeScript/blob/f82d0cb3299c04093e3835bc7e29f5b40475f586/src/compiler/moduleNameResolver.ts#L1049
+        if (keyPrefix) {
+          if (!specifier.startsWith(keyPrefix))
+            continue;
+          matchedPartOfSpecifier = matchedPartOfSpecifier.substring(keyPrefix.length, matchedPartOfSpecifier.length);
+        }
+        if (keySuffix) {
+          if (!specifier.endsWith(keySuffix))
+            continue;
+          matchedPartOfSpecifier = matchedPartOfSpecifier.substring(0, matchedPartOfSpecifier.length - keySuffix.length);
+        }
+      } else {
+        if (specifier !== key)
+          continue;
+        matchedPartOfSpecifier = specifier;
+      }
+
       for (const value of values) {
-        const valueHasStar = value[value.length - 1] === '*';
-        let candidate = valueHasStar ? value.substring(0, value.length - 1) : value;
-        if (valueHasStar && keyHasStar)
-          candidate += specifier.substring(key.length - 1);
+        let candidate: string = value;
+
+        if (value.includes('*'))
+          candidate = candidate.replace('*', matchedPartOfSpecifier);
         candidate = path.resolve(tsconfig.absoluteBaseUrl, candidate.replace(/\//g, path.sep));
         for (const ext of ['', '.js', '.ts', '.mjs', '.cjs', '.jsx', '.tsx']) {
-          if (fs.existsSync(candidate + ext))
-            return candidate;
+          if (fs.existsSync(candidate + ext)) {
+            if (keyPrefix.length > longestPrefixLength) {
+              longestPrefixLength = keyPrefix.length;
+              pathMatchedByLongestPrefix = candidate;
+            }
+          }
         }
       }
     }
+    if (pathMatchedByLongestPrefix)
+      return pathMatchedByLongestPrefix;
   }
   if (specifier.endsWith('.js')) {
     const resolved = path.resolve(path.dirname(filename), specifier);
diff --git a/tests/playwright-test/resolver.spec.ts b/tests/playwright-test/resolver.spec.ts
index 6d36cd5191..98a33aa4cc 100644
--- a/tests/playwright-test/resolver.spec.ts
+++ b/tests/playwright-test/resolver.spec.ts
@@ -163,3 +163,110 @@ test('should respect baseurl w/o paths', async ({ runInlineTest }) => {
   expect(result.passed).toBe(1);
   expect(result.output).not.toContain(`Could not`);
 });
+
+test('should respect complex path resolver', async ({ runInlineTest }) => {
+  const result = await runInlineTest({
+    'playwright.config.ts': `
+      export default {
+        projects: [{name: 'foo'}],
+      };
+    `,
+    'tsconfig.json': `{
+      "compilerOptions": {
+        "target": "ES2019",
+        "module": "commonjs",
+        "lib": ["esnext", "dom", "DOM.Iterable"],
+        "baseUrl": ".",
+        "paths": {
+          "prefix-*": ["./prefix-*/bar"],
+          "prefix-*-suffix": ["./prefix-*-suffix/bar"],
+          "*-suffix": ["./*-suffix/bar"],
+          "no-star": ["./no-star-foo"],
+          "longest-*": ["./this-is-not-the-longest-prefix"],
+          "longest-pre*": ["./this-is-the-longest-prefix"],
+          "*bar": ["./*bar"],
+          "*[bar]": ["*foo"],
+        },
+      },
+    }`,
+    'a.spec.ts': `
+      import { foo } from 'prefix-matchedstar';
+      const { test } = pwt;
+      test('test', ({}, testInfo) => {
+        expect(testInfo.project.name).toBe(foo);
+      });
+    `,
+    'prefix-matchedstar/bar/index.ts': `
+      export const foo: string = 'foo';
+    `,
+    'b.spec.ts': `
+      import { foo } from 'prefix-matchedstar-suffix';
+      const { test } = pwt;
+      test('test', ({}, testInfo) => {
+        expect(testInfo.project.name).toBe(foo);
+      });
+    `,
+    'prefix-matchedstar-suffix/bar.ts': `
+      export const foo: string = 'foo';
+    `,
+    'c.spec.ts': `
+      import { foo } from 'matchedstar-suffix';
+      const { test } = pwt;
+      test('test', ({}, testInfo) => {
+        expect(testInfo.project.name).toBe(foo);
+      });
+    `,
+    'matchedstar-suffix/bar.ts': `
+      export const foo: string = 'foo';
+    `,
+    'd.spec.ts': `
+      import { foo } from 'no-star';
+      const { test } = pwt;
+      test('test', ({}, testInfo) => {
+        expect(testInfo.project.name).toBe(foo);
+      });
+    `,
+    './no-star-foo.ts': `
+      export const foo: string = 'foo';
+    `,
+    'e.spec.ts': `
+      import { foo } from 'longest-prefix';
+      const { test } = pwt;
+      test('test', ({}, testInfo) => {
+        expect(testInfo.project.name).toBe(foo);
+      });
+    `,
+    './this-is-the-longest-prefix.ts': `
+      // this module should be resolved as it matches by a longer prefix
+      export const foo: string = 'foo';
+    `,
+    './this-is-not-the-longest-prefix.ts': `
+      // This module should't be resolved as it matches by a shorter prefix
+      export const bar: string = 'bar';
+    `,
+    'f.spec.ts': `
+      import { foo } from 'barfoobar';
+      const { test } = pwt;
+      test('test', ({}, testInfo) => {
+        expect(testInfo.project.name).toBe(foo);
+      });
+    `,
+    'barfoobar.ts': `
+      export const foo: string = 'foo';
+    `,
+    'g.spec.ts': `
+      import { foo } from 'foo/[bar]';
+      const { test } = pwt;
+      test('test', ({}, testInfo) => {
+        expect(testInfo.project.name).toBe(foo);
+      });
+    `,
+    'foo/foo.ts': `
+      export const foo: string = 'foo';
+    `,
+  });
+
+  expect(result.passed).toBe(7);
+  expect(result.exitCode).toBe(0);
+  expect(result.output).not.toContain(`Could not`);
+});