If you’re trying to scrub old content from Google, your first step depends on...

https://www.contentgrip.com/delete-outdated-google-search-results/

If you’re trying to scrub old content from Google, your first step depends on who owns the site. If you control the URL, delete the page and ensure it returns a true 404 status. Use Google’s "Refresh Outdated Content" tool to signal the change