diff --git a/package-lock.json b/package-lock.json
index bd1c129..169ef08 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -9,7 +9,7 @@
       "version": "3.0.1",
       "license": "MIT",
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@@ -164,95 +164,6 @@
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@@ -288,15 +199,6 @@
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@@ -390,6 +294,18 @@
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+      "funding": {
+        "url": "https://github.com/sponsors/jonschlinkert"
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@@ -1609,21 +1525,6 @@
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@@ -1746,28 +1647,6 @@
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@@ -3243,6 +3049,18 @@
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+      "dev": true,
+      "engines": {
+        "node": ">=8.6"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/jonschlinkert"
+      }
+    },
     "node_modules/reflect.getprototypeof": {
       "version": "1.0.6",
       "resolved": "https://registry.npmjs.org/reflect.getprototypeof/-/reflect.getprototypeof-1.0.6.tgz",
@@ -3543,6 +3361,7 @@
       "version": "2.0.0",
       "resolved": "https://registry.npmjs.org/shebang-command/-/shebang-command-2.0.0.tgz",
       "integrity": "sha512-kHxr2zZpYtdmrN1qDjrrX/Z1rR1kG8Dx+gkpK1G4eXmvXswmcE1hTWBWYUzlraYw1/yZp6YuDY77YtvbN0dmDA==",
+      "dev": true,
       "dependencies": {
         "shebang-regex": "^3.0.0"
       },
@@ -3554,6 +3373,7 @@
       "version": "3.0.0",
       "resolved": "https://registry.npmjs.org/shebang-regex/-/shebang-regex-3.0.0.tgz",
       "integrity": "sha512-7++dFhtcx3353uBaq8DDR4NuxBetBzC7ZQOhmTQInHEd6bSrXdiEyzCvG07Z44UYdLShWUyXt5M/yhz8ekcb1A==",
+      "dev": true,
       "engines": {
         "node": ">=8"
       }
@@ -3576,17 +3396,6 @@
         "url": "https://github.com/sponsors/ljharb"
       }
     },
-    "node_modules/signal-exit": {
-      "version": "4.1.0",
-      "resolved": "https://registry.npmjs.org/signal-exit/-/signal-exit-4.1.0.tgz",
-      "integrity": "sha512-bzyZ1e88w9O1iNJbKnOlvYTrWPDl46O1bG0D3XInv+9tkPrxrN8jUUTiFlDkkmKWgn1M6CfIA13SuGqOa9Korw==",
-      "engines": {
-        "node": ">=14"
-      },
-      "funding": {
-        "url": "https://github.com/sponsors/isaacs"
-      }
-    },
     "node_modules/standard": {
       "version": "17.1.0",
       "resolved": "https://registry.npmjs.org/standard/-/standard-17.1.0.tgz",
@@ -3996,20 +3805,7 @@
       "version": "4.2.3",
       "resolved": "https://registry.npmjs.org/string-width/-/string-width-4.2.3.tgz",
       "integrity": "sha512-wKyQRQpjJ0sIp62ErSZdGsjMJWsap5oRNihHhu6G7JVO/9jIB6UyevL+tXuOqrng8j/cxKTWyWUwvSTriiZz/g==",
-      "dependencies": {
-        "emoji-regex": "^8.0.0",
-        "is-fullwidth-code-point": "^3.0.0",
-        "strip-ansi": "^6.0.1"
-      },
-      "engines": {
-        "node": ">=8"
-      }
-    },
-    "node_modules/string-width-cjs": {
-      "name": "string-width",
-      "version": "4.2.3",
-      "resolved": "https://registry.npmjs.org/string-width/-/string-width-4.2.3.tgz",
-      "integrity": "sha512-wKyQRQpjJ0sIp62ErSZdGsjMJWsap5oRNihHhu6G7JVO/9jIB6UyevL+tXuOqrng8j/cxKTWyWUwvSTriiZz/g==",
+      "dev": true,
       "dependencies": {
         "emoji-regex": "^8.0.0",
         "is-fullwidth-code-point": "^3.0.0",
@@ -4098,18 +3894,7 @@
       "version": "6.0.1",
       "resolved": "https://registry.npmjs.org/strip-ansi/-/strip-ansi-6.0.1.tgz",
       "integrity": "sha512-Y38VPSHcqkFrCpFnQ9vuSXmquuv5oXOKpGeT6aGrr3o3Gc9AlVa6JBfUSOCnbxGGZF+/0ooI7KrPuUSztUdU5A==",
-      "dependencies": {
-        "ansi-regex": "^5.0.1"
-      },
-      "engines": {
-        "node": ">=8"
-      }
-    },
-    "node_modules/strip-ansi-cjs": {
-      "name": "strip-ansi",
-      "version": "6.0.1",
-      "resolved": "https://registry.npmjs.org/strip-ansi/-/strip-ansi-6.0.1.tgz",
-      "integrity": "sha512-Y38VPSHcqkFrCpFnQ9vuSXmquuv5oXOKpGeT6aGrr3o3Gc9AlVa6JBfUSOCnbxGGZF+/0ooI7KrPuUSztUdU5A==",
+      "dev": true,
       "dependencies": {
         "ansi-regex": "^5.0.1"
       },
@@ -4349,6 +4134,7 @@
       "version": "2.0.2",
       "resolved": "https://registry.npmjs.org/which/-/which-2.0.2.tgz",
       "integrity": "sha512-BLI3Tl1TW3Pvl70l3yq3Y64i+awpwXqsGBYWkkqMtnbXgrMD+yj7rhW0kuEDxzJaYXGjEW5ogapKNMEKNMjibA==",
+      "dev": true,
       "dependencies": {
         "isexe": "^2.0.0"
       },
@@ -4470,23 +4256,6 @@
         "url": "https://github.com/chalk/wrap-ansi?sponsor=1"
       }
     },
-    "node_modules/wrap-ansi-cjs": {
-      "name": "wrap-ansi",
-      "version": "7.0.0",
-      "resolved": "https://registry.npmjs.org/wrap-ansi/-/wrap-ansi-7.0.0.tgz",
-      "integrity": "sha512-YVGIj2kamLSTxw6NsZjoBxfSwsn0ycdesmc4p+Q21c5zPuZ1pl+NfxVdxPtdHvmNVOQ6XSYG4AUtyt/Fi7D16Q==",
-      "dependencies": {
-        "ansi-styles": "^4.0.0",
-        "string-width": "^4.1.0",
-        "strip-ansi": "^6.0.0"
-      },
-      "engines": {
-        "node": ">=10"
-      },
-      "funding": {
-        "url": "https://github.com/chalk/wrap-ansi?sponsor=1"
-      }
-    },
     "node_modules/wrappy": {
       "version": "1.0.2",
       "resolved": "https://registry.npmjs.org/wrappy/-/wrappy-1.0.2.tgz",
diff --git a/package.json b/package.json
index e010544..69f6a2a 100644
--- a/package.json
+++ b/package.json
@@ -46,7 +46,7 @@
     "url": "git://github.com/asciidoctor/opal-node-runtime.git"
   },
   "dependencies": {
-    "glob": "10.4.2",
+    "picomatch": "4.0.2",
     "unxhr": "1.2.0"
   },
   "devDependencies": {
diff --git a/spec/main.spec.js b/spec/main.spec.js
index f16dd0d..0623b3b 100644
--- a/spec/main.spec.js
+++ b/spec/main.spec.js
@@ -60,5 +60,12 @@ describe('Opal Node Runtime', function () {
       const currentDir = Dir.$pwd()
       expect(currentDir).to.equal(process.cwd().replace(/\\/g, '/'))
     })
+    it('should list files using Dir.glob', function () {
+      Opal.load('nodejs')
+      const Dir = Opal.const_get_relative([], 'Dir')
+      const workingDirectory = process.cwd().replace(/\\/g, '/')
+      const result = Dir.$glob(`${workingDirectory}/*.md`)
+      expect(result).to.deep.equal(["README.md"])
+    })
   })
 })
diff --git a/src/nodejs.js b/src/nodejs.js
index e1fd7a6..653b0fb 100644
--- a/src/nodejs.js
+++ b/src/nodejs.js
@@ -1,7 +1,7 @@
 import __fs__ from 'fs';
 import __path__ from 'path';
 import __util__ from 'util';
-import { glob as __glob__ } from 'glob';
+import __pm__ from 'picomatch';
 import __os__ from 'os';
 import __xmlhttprequest__ from 'unxhr';
 
@@ -746,29 +746,32 @@ Opal.modules["nodejs/dir"] = function(Opal) {/* Generated by Opal 1.7.3 */
     var self = $klass($base, $super, 'Dir');
 
     var $nesting = [self].concat($parent_nesting);
-    if (self.__glob__ == null) self.__glob__ = nil;
+    if (self.__pm__ == null) self.__pm__ = nil;
     if (self.__fs__ == null) self.__fs__ = nil;
     if (self.__path__ == null) self.__path__ = nil;
     if (self.__os__ == null) self.__os__ = nil;
 
-    
-    self.__glob__ = __glob__;
+
+    function pwd() {
+      return process.cwd().split(__path__.sep).join(__path__.posix.sep)
+    }
+
+    self.__pm__ = __pm__;
     self.__fs__ = __fs__;
     self.__path__ = __path__;
     self.__os__ = __os__;
     return (function(self, $parent_nesting) {
       var $nesting = [self].concat($parent_nesting), $$ = Opal.$r($nesting);
 
-      
-      
-      $def(self, '$[]', function $$$1(glob) {
-        
-        return __glob__.sync(glob)
+      $def(self, '$[]', function $$$1(pattern) {
+        var self = this
+
+        return self.$glob(pattern)
       });
       
       $def(self, '$pwd', function $$pwd() {
-        
-        return process.cwd().split(__path__.sep).join(__path__.posix.sep);
+
+        return pwd();
       });
       
       $def(self, '$home', function $$home() {
@@ -797,22 +800,45 @@ Opal.modules["nodejs/dir"] = function(Opal) {/* Generated by Opal 1.7.3 */
         return result;
       
       });
-      
-      $def(self, '$glob', function $$glob(pattern) {
-        
-        
-        if (!$truthy(pattern['$respond_to?']("each"))) {
+
+      $def(self, '$glob', function $$glob (pattern) {
+        if (!$truthy(pattern['$respond_to?']('each'))) {
           pattern = [pattern]
-        };
-        return $send(pattern, 'flat_map', [], function $$2(subpattern){
-          
-          if (subpattern == null) subpattern = nil;
-          if ($truthy(subpattern['$respond_to?']("to_path"))) {
+        }
+        pattern = $send(pattern, 'map', [], function $$2 (subpattern) {
+          if (subpattern == null) subpattern = nil
+          if ($truthy(subpattern['$respond_to?']('to_path'))) {
             subpattern = subpattern.$to_path()
-          };
-          subpattern = $Opal['$coerce_to!'](subpattern, $$('String'), "to_str");
-          return __glob__.sync(subpattern);;});
-      });
+          }
+          return $Opal['$coerce_to!'](subpattern, $$('String'), 'to_str')
+        })
+        return pattern.flatMap((subpattern) => {
+          const scanResult = __pm__.scan(subpattern)
+          let base = scanResult.negated || scanResult.base === ''
+            ? pwd()
+            : scanResult.base
+          try {
+            const stat = __fs__.statSync(base)
+            if (stat.isFile()) {
+              base = __path__.dirname(base)
+            }
+          } catch (e) {
+            if (e.code === 'ENOENT' || e.code === 'EACCES' || e.code === 'ENOTDIR') {
+              return []
+            }
+          }
+          try {
+            const files = __fs__.readdirSync(base, { recursive: true })
+            const isMatch = __pm__(subpattern, { windows: true })
+            return files.filter(f => isMatch(__path__.join(base, f)))
+          } catch (e) {
+            if (e.code === 'ENOENT' || e.code === 'EACCES' || e.code === 'ENOTDIR') {
+              return []
+            }
+            throw e
+          }
+        })
+      })
       return $alias(self, "getwd", "pwd");
     })(Opal.get_singleton_class(self), $nesting);
   })($nesting[0], null, $nesting)
diff --git a/update.cjs b/update.cjs
index ec4c699..67d5302 100644
--- a/update.cjs
+++ b/update.cjs
@@ -53,9 +53,9 @@ if (!nodejsSource.includes('import __fs__ from \'fs\';')) {
     // util
     .replace(/self\.__util__ = require\('util'\);/g, 'self.__util__ = __util__;')
     .replace(/\s+var __util__ = self\.__util__;/g, '')
-    // glob
-    .replace(/self\.__glob__ = require\('glob'\);/g, 'self.__glob__ = __glob__;')
-    .replace(/\s+var __glob__ = self\.__glob__;/g, '')
+    // picomatch
+    .replace(/self\.__pm__ = require\('picomatch'\);/g, 'self.__pm__ = __pm__;')
+    .replace(/\s+var __pm__ = self\.__pm__;/g, '')
     // os
     .replace(/self\.__os__ = require\('os'\);/g, 'self.__os__ = __os__;')
     .replace(/\s+var __os__ = self\.__os__;/g, '')
@@ -64,7 +64,7 @@ if (!nodejsSource.includes('import __fs__ from \'fs\';')) {
   fs.writeFileSync(nodejsSourceFile, `import __fs__ from 'fs';
 import __path__ from 'path';
 import __util__ from 'util';
-import { glob as __glob__ } from 'glob';
+import __pm__ from 'picomatch';
 import __os__ from 'os';
 import __xmlhttprequest__ from 'unxhr';