What's the most "feels bad for the enemy team" moment you've had?

We were against a Klepto Karma top lane with the Spellthief's Edge start, basically the zero CS strategy. Only issue is, this was literally one patch AFTER they implemented the 'only get gold if an ally's nearby' fix. I only realized it when we were at around 10 minutes or so when everyone had around 60 to 80 cs and she literally had zero. I felt so bad I tried telling him on allchat but I don't think he ever got the message and ended the game with under 40 or so cs.

Poor guy..(literally???)