After a 5th time around, this format is getting tired. Here is my suggestion on how to spice things up:
-Have the skaters play a round of skate, like normal.
-Once one skater wins, bring out an Element brand (TM) high ollie bar
-Start the bar high and go backwards in height
-Whoever can't ollie it when the other skater can is eliminated
That'll make it wayyy better.