I remember a successful challenge, it was in U12's, maybe 10 years ago. Mornington had an unexpectedly dominant team & were granted a challenge against Dandenong 1, it went into OT from memory & Mornington won.
I felt very sorry for the Dandenong team, they had won their crossover on the Friday night (which should've secured their spot in VC), only to have to front up on Sunday for the challenge (they were clearly deflated). I think their winning margin was the least & that's why they had to play the challenge & not one of the other teams who had also won their way through on the previous Friday night.