When clearing outdated search results, your approach depends on site ownership....

https://www.save-bookmarks.win/getting-rid-of-outdated-google-search-results-depends-on-one-thing-do-you

When clearing outdated search results, your approach depends on site ownership. If you own the site, delete the content and ensure it returns a proper 404 status; don't rely on "soft" errors that keep pages indexed