Once a Challenger is fully declined a fight, s/he can never again be resought for the same later on. The maximum you can pay for rematch is 30 gems.
For every rematch you will need more gems. If the player loses, he will be given two options one, to simply leave, two, to try again with x amount of gems. Other rewards are fight bonus and small amounts of XP.
Upon their defeat the Challengers give up their enchanted weapons to Shadow which he may now use for his battles. The fight takes place in the location of where the Duels of that Act would. The Challengers initiate a special mode of fight that works exactly like a single stage of Tournament having a maximum of three rounds timed 99 seconds where the player has the freedom to use his/her own equipment and does not feature any altered rules or conditions. Whenever Shadow may encounter any of them, the fight difficulty is always displayed as Insane and the player must get a least few upgrades on the equipment in order secure a win. Challengers are skilled fighters that appear in Shadow Fight 2 exclusively to challenge Shadow having heard of his remarkable skills and merely wishing a good fight.