Career
He has played for a number of clubs in Colombia, Argentina, Spain, Cyprus and Uruguay. In 2003 he went back to Argentina to play for Club Atlético Independiente. He then had spells in Europe with Real Valladolid of Spain and AEL Limassol of Cyprus, In 2008 he joined Defensor Sporting of Uruguay.
Castillo returned to Argentina in 2008 to play for newly promoted Godoy Cruz, he scored twice on his league debut against Banfield and then on 28 September 2008 he scored a hat-trick helping Godoy Cruz to beat Boca Juniors 4–1.
The next game, on 5 October 2008, away to Gimnasia (J), Jairo suffered a season-ending torn Anterior Cruciate Ligament in a hard tackle. Godoy Cruz subsequently lost their next 3 games.
In September 2009, after 11 months without playtime, Jairo Castillo left Godoy Cruz after his contract with the club from Mendoza expired, and joined the ranks of Millonarios, in Bogotá, Colombia. In December 2009 the 32-year-old forward Jairo Fernando Castillo Cortés moved back to Godoy Cruz after six months in Colombia.