What was probably our worst experience was during our rookie year, very first FRC competition we'd ever been to.
We were all psyched and ready to go, eager to take on LogoMotion and all it had to offer. We were excited by the harsher (and larger) competition in comparison to OCCRA. Everything looked great.
And then we got our robot inspected: It was 32 pounds overweight!

We had to rip that thing apart in under an hour to get re-inspected without the armature or superstructure. Our robot was nothing more than a chassis with a minibot that kept falling out and nearly getting crushed by other robots on the field for the entire weekend. On the bright side, though, we shaved off the extra weight during that competition, and had a fully-functioning machine by the next weekend's event.
This year, our robot got completely flipped upside-down at IRI, which damaged the shooter's motor pretty badly. Our robot was fairly low to the ground and agile, but because of the placement of the climber, it had a tendency to (as we like to jokingly call it) "do the Harlem Shake" whenever it came to an abrupt stop. So during our final match, the robot was fully loaded and flying across the field at full speed, but another robot intercepted it, so our driver had to stop suddenly. Well... the intercepting robot (from the opposing alliance) bashed into our robot's front bumper as it was teetering back and forth, sending the thing belly-up for the first time.