fix #35935

src/vs/code/electron-main/menus.ts

@@ -467,10 +467,20 @@ export class CodeMenu {
 		}
 
 		if (workspaces.length || files.length) {
+			const hasNoWindows = (this.windowsMainService.getWindowCount() === 0);
+
 			openRecentMenu.append(__separator__());
 			openRecentMenu.append(this.createMenuItem(nls.localize({ key: 'miMore', comment: ['&& denotes a mnemonic'] }, "&&More..."), 'workbench.action.openRecent'));
 			openRecentMenu.append(__separator__());
-			openRecentMenu.append(new MenuItem(this.likeAction('workbench.action.clearRecentFiles', { label: this.mnemonicLabel(nls.localize({ key: 'miClearRecentOpen', comment: ['&& denotes a mnemonic'] }, "&&Clear Recently Opened")), click: () => this.historyMainService.clearRecentlyOpened() })));
+
+			let clearRecentFiles: MenuItem;
+			if (hasNoWindows) {
+				clearRecentFiles = new MenuItem(this.likeAction('workbench.action.clearRecentFiles', { label: this.mnemonicLabel(nls.localize({ key: 'miClearRecentOpen', comment: ['&& denotes a mnemonic'] }, "&&Clear Recently Opened")), click: () => this.historyMainService.clearRecentlyOpened() }));
+			} else {
+				clearRecentFiles = this.createMenuItem(nls.localize({ key: 'miClearRecentOpen', comment: ['&& denotes a mnemonic'] }, "&&Clear Recently Opened"), 'workbench.action.clearRecentFiles');
+			}
+
+			openRecentMenu.append(clearRecentFiles);
 		}
 	}