of the season in a 1–1 home draw against Hearts on 22 January, scoring the first goal of the match in the 54th minute. He made one Cup appearance in a 2–0 away defeat against Hibernian on 8 January. Caballero finished the season with 1 goal in 29 appearances in all competitions. Dundee finished in 12th position of the SPL table, with 33 points, and were subsequently relegated to the Scottish First Division for the 2005–06 season. Caballero was released by the club on 23 May 2005. Olimpia Asunción In July 2005, Caballero returned to Paraguay to join Olimpia Asunción for the 2005 Paraguayan Primera División season. On 27 July, he first appeared for Olimpia in a friendly match against Fénix which ended 0–0 in Montevideo. He was not taken into account by the club's first-team coach and decided to see if he could play for the club's reserve-team. During a meeting with Olimpia's president, Caballero expressed his desire to play and stated that the year was ending Latter career In January 2006, he was transferred to Club Tacuary for the 2006 Paraguayan Primera División season, Caballero made just two league appearances, however, Tacuary qualified for the 2007 Copa Libertadores as the best finisher in the aggregate points table and the 2007 Copa Sudamericana by winning the 2006 Liguilla Pre-Sudamericana. In January 2007, Caballero joined K League club Daejeon Citizen FC, making 6 league appearances. In July 2007, he was released from the club and signed for Cypriot club Alki Larnaca for the first half of the 2007–08 season. In January 2008, Caballero signed with Chilean outfit Provincial Osorno for the 2008 Chilean Primera División season. 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. He participated in the 2010 Paraguayan Primera División season, scoring 4 goals (including a double in a 3–0 away victory against former club Tacuary on 16 May) in 26 appearances, and also participated in the 2010 Copa Libertadores, making two appearances (one appearance in