The I-League 2008–2009 season began on 26 September 2008 and finished on 16 April 2009 with a break in December for the Federation Cup and Durand Cup. Most games this season were played on Saturday's and Sunday's to attract larger crowds. After a successful first season for the I League, the second season featured 12 teams from four cities – again this would be expanded in the 2009–10 season to 14 teams. The champion in the I-League qualified for the AFC Champions League 2010 qualifying playoffs in 2010, while the bottom two teams were relegated to I-League 2nd Division for the next season.