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Yes trainers can rematch you in Pokemon crystal but you must register there phone numbers to do that but not all trainers will rematch you, wait until the trainers call you they will mention they want to battle again and they will remind you where they are go there and talk to the trainer to battle them again. They can keep calling you for rematches throughout the game don't miss the chance to rematch them.
There is no vs seeker in ruby, use your pokenav to check trainers eyes this page will show pokeballs near trainers that want to rematch you talk to those trainers to rematch them.
you battle trainers again by adding them onto your pokegear and then soon they will want a rematch
No
At any random time..actually..keep calling them in ur pokenav!