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Cloud
Defeating Cloud isn't easy, you'll first encounter him when you enter the first tourement. If visited the Coliseum straight after exiting Traverse town then Cloud will be nearly impossible to beat let alone reach.
Instead of fighting and fighting until you win I suggest you visit either Wonderland or Deep Jungle. After completing either of these worlds you should be a higher level and able to defeat all the enemies that lead up to Cloud.
When fighting Cloud there is one vital strategy, keep attacking - just keep on hitting Cloud with everything you've got and not letting him strike back, you should win the fight in no time! ^_^
Hercules
After visiting all the Key Holes then three new matches will appear. Select Hercules Cup and fight your way through the enemies, along the way you'll have to battle Cloud (if you win you get the Metal Chocobo! ^_^) once you've finally reached Hercules he won't attack often but he has a shield, the only way to break the shield is to throw a barrel at him (either choose lift or strike), once the shield has vanished just full on attack him with everything you've got!