 Upon Caballero's return to Dundee, his first appearance of the 2004–05 Scottish Premier League season came in a 1–1 away draw against Aberdeen on 2 October, where he was substituted onto the field for John Sutton in the 77th minute.A fortnight after his regression to Dundee, Caballero returned to Paraguay to deal with a personal matter.First-team coach, Jim Duffy, who had told Caballero that he could have waited until after Dundee's 3–1 win over Kilmarnock to travel, expected Caballero to return by the following week and focused on his football and respectively described Caballero as a "the type of guy that, when he has a problem, he has to deal with it immediately".