Several stories immediately come to mind at the topic.
1) So, I fancy myself as a fairly skilled medic. My best mate is a damn good spy. Now, this story takes place in the first round of the ETF2L Highlander tournament a few months ago. It was dustbowl, the second stage, final point. We were RED. I had just seen every one of my teammates die, and the other guys get on the point, about to cap. So, naturally, uber ready, I charge the point, just hoping to hold them off long enough for my teammates to respawn. I charge at the point and see a flash of red in the corner of the screen. On reflex, I click on it and uber it. Turns out, it was my friend, our spy. Together, we ran on to the point. He backstabbed two of them before the others knew what was going on, and he got two more as they ran off. Four people, fully armed, running from a medic and a spy. We actually ended up winning that round.
2) So, I also fancy myself as a fairly skilled demoman. Never is this more apparent, oddly enough, than when I play on ctf_2fort. I have a habit of just sticky-jumping between the battlements, nabbing the intel, and sticky-jumping back. However, one time, I didn't have enough health to get to the battlements, and pursuit had led me to the lower level, by the bridge. As I run out of the doors to the courtyard, I see a mini-sentry, right in front of me. It turns towards me, beeping with indignation that I would dare to challenge it--and exploded. I stood there for a moment, not quite sure that that had really happened. Turns out, the other team's engie chose just the right moment to destroy his sentry. I mentioned this over the mic, and he got pissed. The whole thing was hilarious.
3) Much shorter one: On Degroot, RED, I once targe'd off the battlements, turned right after the charge ended, and whacked at a soldier. I was wielding the half-zatoichi. The guy went flying, for no reason at all. He died from falling off the cliff a second later. I still don't know what happened.
