2006. Indiana Robotics Invitational. We had 2-speed pneumatically-shifted transmissions. The opposing alliance, we knew, would go straight over to the low goal and dump, so our plan was to sprint over to that wall at our top speed (something like 15ft/s that year

) and shift down with only a few feet left. Tested in the pit; it worked great. Put the 'bot out on the field for quarterfinals, it sprinted across and totally neglected to shift. It slammed into the wall going 15ft/s, causing the whole robot to spin about 135 degrees to the right, and causing the main battery to break free of its Velcro mounting and disconnect from the robot, leaving us parked there for the rest of the match. It was my program that did this...and I still to this day have no explanation of what happened.
2007. IRI yet again. We were doing exceptionally well and made it into the finals. First out of three matches..we won; this match was not very eventful. Second match...the scores are so close...and a bit of pneumatic tubing on our arm cancelled our bonus points, causing us to lose the match. Third match, about 15 seconds into teleop, we run into the opposing alliance wall and...no response. On closer inspection post-match, our radio had come unplugged--nobody ever screwed it in.
2008. Great Lakes Regional. My autonomous code delays, as it is supposed to. Our partner (I don't remember who it was anymore...it was a practice match) drove out and was hovering slowly around the overpass; I think they were using a camera or something...they were attempting to knock down a ball. My code dutifully ticks off the second and a half delay, then drives forward. The partner's forklift is up above the overpass. We plow into the back of them, and continue pushing until they are laying on the floor sideways.

That was a fun match...
Also this year, more than once we would get off-course but the code wouldn't sense it, and would faithfully count off gear-tooth sensor clicks--so we would be running into the center wall, the wheels would scrub enough so that it looked like we had travelled far enough cross-ways, and then it would start the 3rd segment run--back towards the alliance station, but since we weren't around the corner, we would run over the line we had already crossed, getting a penalty before the humans had a chance to touch it.
EDIT: In 2006, I did not personally get the pleasure of witnessing
this event, but it looks like it was quite entertaining and smelly...