Ash meets Brock in episode 5 of season 1, Showdown in Pewter City.
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well actually he never leaves if you saw the episode ash meets brock he says he needs someone to go with and ash volunteers so he stays with him forever
When Ash battled and defeted Brock (harldy fair) in Pewter Gym, Brock decided to tag along with Ash to his journey.
Yes, May returns during the Sinnoh season for the Wallace Cup competition where she meets up with Ash and Brock again.
If you are talking about after the Johto League tournament, yeah. They meet in episode 319. :D
ash never catches a mudkip he catches a treeco but Brock catches a mudkip