 Caballero scored 3 goals in 15 league appearances for Osorno, in 2–0 away victory against Huachipato on 3 February, a 3–1 home victory against Melipilla on 3 March, and in a 3–1 home defeat against Concepción on 23 March.In June 2008, Caballero signed with Greek club Panachaiki for the 2007–08 Gamma Ethniki season, where he was coached by Australian coach Ange Postecoglou.In January 2010, Caballero signed with Nacional Asunción, where he was reunited with coach Ever Hugo Almeida.