Not with cycling, but I played goalie in an adult soccer league for years.
One season, the week before the playoffs started, I broke my index finger and dislocated my thumb. Prior to the next week's game, my wife insisted that I switch positions with another player, which I did...
...until halftime. We were down 2-1, the guy in goal was toast and begged me to switch back with him. I had already cut away a big chunk of the cast to accommodate riding my bike to work but still couldn't get my goalie glove over it. I played keeper for the second half.
We ended up winning 4-2. However, I broke two more fingers and had to call my wife from the ER.