If you’re stuck with outdated Google results, the fix depends on whether you...

https://reportz.io/technology/how-do-i-keep-dead-urls-from-creating-a-bad-user-experience-in-search/

If you’re stuck with outdated Google results, the fix depends on whether you control the site. If you own it, delete the content and ensure it returns a true 404 error; don't leave "soft 404s" that confuse search engines