We discussed in Chat how some of these events might go with 10 people. For example, in penalty kicks, each participant would take 9 shots; one shot against every other participant. It's the only way to ensure that everybody faces the same quality of goaltending. I'd definitely recommend having each person take all 9 kicks in a row though rather than having everybody take kick #1, then kick #2, etc. The speed of the game would be improved by the extra players able to stand behind the net, as the kicker wouldn't have to chase his own ball down and switch positions after each kick. Also, we could bring a 2nd ball to speed things up further.
For HRD, it probably doesn't matter as much who pitches, so as long as the batter is happy with his pitcher, it'll work fine. Everybody should be allowed to choose their own pitcher or switch pitchers if they don't like the pitches they're seeing.
40 Yard Dash, Free throws, and Football Toss are still easy, as are Vertical Leaps, Long Jumps, and Chin-Ups if people want to keep those.
Arm wrestling is obviously out of the question but Sumo could still possibly work as a 10-man game. We'd just need a bigger circle and each round would be a huge free-for-all. I'd actually be interested in seeing how that works out!
Edit - And another thing! The penalty kicks could potentially be 2 challenges in one. We could be ranked by goals scored and also by goals given up. Of course there's some correlation between the two events, as scoring goals also helps you in the goaltending competition and vice versa, but I think that's a minor consideration.