Clearing old, embarrassing search results comes down to one question: do you...

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

Clearing old, embarrassing search results comes down to one question: do you control the site? If it’s your site, fix the page and use Google’s "Refresh Outdated Content" tool to update the snippet