If you need to scrub outdated search results, the right approach depends on...

https://www.ready-bookmarks.win/when-your-search-results-are-cluttered-with-old-irrelevant-pages-the-fix

If you need to scrub outdated search results, the right approach depends on whether you control the website. Use Google’s "Refresh Outdated Content" tool for pages you don’t own that have already changed