2001 | World Cup | FIFA World Cup | UEFA Champions League | 2010 FIFA World Cup | FA Cup | 2001 in music | 1978 FIFA World Cup | UEFA Europa League | 2006 FIFA World Cup | Davis Cup | Stanley Cup | Rugby World Cup | UEFA | Cricket World Cup | 1986 FIFA World Cup | 1982 FIFA World Cup | 2001 ATP Tour | Sprint Cup Series | 2007 Cricket World Cup | 2011 Rugby World Cup | 2002 FIFA World Cup | UEFA Euro 2012 | League Cup | 2001: A Space Odyssey | Scottish Cup | Grey Cup | Football League Cup | 1998 FIFA World Cup | Challenge Cup |
After a brief return to Paraguay with Sol de América, Caballero signed with Scottish Premier League club Dundee F.C. from 2000 to 2005, with whom he played for in the 2001 UEFA Intertoto Cup and finished as runners-up in the 2002–03 Scottish Cup, after a 1–0 loss against Rangers F.C. in the final on 31 May 2003.