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Kerr won four bouts between Pride 2 and Pride 6. However, his status was soon questioned after his first bout with Igor Vovchanchyn at Pride 7, in which he was knocked out by illegal knee strikes. Even though the loss was overturned and changed to a "No Contest" ruling, Kerr admitted that the initial loss had been a difficult decision for him to face. Following his fight against Vovchanchyn, Kerr fought in the Pride Grand Prix 2000 Opening Round and won over Enson Inoue. His win against Inoue earned him a place at the Pride Grand Prix 2000 Finals, where he fought Kazuyuki Fujita and lost by decision. At Pride 10 - Return of the Warriors Kerr defeated Igor Borisov by submission. Four months later, at Pride 12 - Cold Fury, he lost by decision in the rematch with Vovchanchyn. Kerr then lost to Heath Herring at Pride 15 via TKO. With his second loss in a row, Kerr decided to take time away from MMA.