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Gladiator doesn't block
At the beginning of Joust, step forward two spaces, then (you must do this before the gladiator gets to the end of their pedestal), push back. You should spin the jousting stick over your head and hit the gladiator. If you do this correctly the gladiator will not block and you will be able to repeatedly hit him in this manner until you win. Don't let go of the B button.