If you’re stuck with outdated Google results, the fix depends on whether you...

https://dibz.me/blog/whats-the-safest-way-to-remove-a-page-without-causing-a-bigger-seo-mess-1073

If you’re stuck with outdated Google results, the fix depends on whether you control the site. If you own it, delete the content and ensure it returns a true 404 error; don't leave "soft 404s" that confuse search engines