Clearing outdated Google results comes down to one question: do you own the...

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

Clearing outdated Google results comes down to one question: do you own the site? If you control the page, update it to a 404 error and use the "Refresh Outdated Content" tool