 On 23 August, Caballero scored a double in a 3–0 home League cup victory against Montrose.Four days later, he scored again in a 1–1 home league match against Hearts on 27 August, the goal being his fifth goal in four consecutive matches.During October 2000, Dundee opted to sign Claudio Caniggia as a replacement for Caballero who had surgery to repair a damaged knee and underwent extensive rehabilitation at a Bologna clinic.