At the start of the 2009–10 season, Caicedo was tipped to leave City in order to get more playing time, especially after the club signed fellow forwards Roque Santa Cruz, Emmanuel Adebayor, and Carlos Tevez. On 23 July 2009, Sporting Clube de Portugal and Manchester City reached an agreement over an initial one-year loan with an option of a permanent deal, that would allow him to be part of their squad for the 2009–10 UEFA Champions League, potentially allowing Caicedo a year to develop himself as a forward before returning to Manchester City. Caicedo made his debut for Sporting CP shirt after coming on as a substitute for Hélder Postiga injured on a 36th minutes in a 2–1 loss against Braga on 22 August 2009. After suffering a Stretched Ligament injury in a match against Braga which he was out of action for 3 weeks, Caicedo made his return for Sporting CP when he provided assist for Simon Vukčević to score a winning goal in a 1–1 draw against S.C. Olhanense on 21 September 2009. Caicedo, however, found it difficult at Sporting and his loan deal was cut short in January 2010.