Early on, he was loaned to Tercera División sides Atlético Arona CF and AD Laguna, in order to gain experience.

[1][2] Santana's performances caught the eye of Hearts manager Csaba László, who signed him on a free transfer from Tenerife on 30 June 2009.

[3] He got off to a good start at Tynecastle Stadium, playing in every pre-season game and particularly impressing in friendlies against Bolton Wanderers (where he set up the only goal) and Sunderland, putting in player of the match performances.

[4] However, in the Scottish Premier League, Santana's displays were somewhat erratic: during a 2–2 draw with St Johnstone, he was replaced after an alleged spitting incident.

[9] Santana's second season in Scotland was hit by injuries, and he never really managed to get a consistent run together, also having to undergo knee surgery in late April 2011.