Kind of random actually. You only got a 33% chance of winning a clash, 33% to lose and the rest to simply pass the turn without anything happening. It is mostly luck based, you can have all the equipment in the world, if you are unlucky you will still lose. Nice idea though, but can become very frustrating if lady luck isn't on your side.
@herbalisk You can use the pipe to knock out the guard at the club entrance, the slot machine to access the secret lab and the heating control to reveal the hatter's secret massage.