Early career Santana started his career in his native country with
San Lorenzo. After his contract with San Lorenzo expired, he decided to try his luck in European football, moving to Italy in January 2002 for
Serie A team
Venezia, then relegated at the end of the season. He then followed his chairman
Maurizio Zamparini to
Serie B team
Palermo, where he showed high qualities in his role. In 2003, he was then loaned to
Serie A side
A.C. ChievoVerona (along with
Stefano Morrone with
Eugenio Corini moved to opposite direction), becoming one of the most interesting wingers in the Italian top division, and being first capped for the Argentina national football team in a friendly match against
Japan on 18 August 2004. He then returned to Palermo, which was just promoted to Serie A at the time, for the following season.
Fiorentina In May 2006, he was signed by
la viola for €6.5 million (€5 million plus 50% of
Parravicini) to prepare for
2006–07 UEFA Champions League 3rd qualifying round. But due to
2006 Serie A scandal, Fiorentina finished 9th and did not qualify for any European competitions. In the 2009–10 season,
La Viola signed
Marco Marchionni, making Santana first became a backup player, likes the first group stage of
2009–10 UEFA Champions League match against
Lyon, substituted Marchionni in the 72 minutes. He started the third group stage match, as Marchionni was rested. In the 4th match, he lost his starting place again to Marchionni. He substituted
Juan Vargas in the 77th minute of that match. In the last two matches of the group stage, Santana played a new role as an attacking midfielder as
Adrian Mutu was rested. In the league, Santana was moved to left midfield position (rotated with Vargas), attacking midfielder, second striker (when Mutu was unavailable and later the coach preferred Jovetić) or right midfielder when Marchionni was rested. Santana initially had a better chance to play after
Martin Jørgensen left in January 2010. On 14 February 2010, Santana was injured on the league match against
Sampdoria, missed the Champions League match against
Bayern Munich. In April 2010, Santana was injured and expected to be out for 5 months after clash with opponent goalkeeper in a club friendly against
San Miniato Basso.
Napoli and loans to Cesena and Torino On 12 July 2011, Santana finally agreed to sign with
Napoli over
Cesena, leaving
Fiorentina after five years. He moved on loan to
A.C. Cesena on 31 January 2012. On 12 July 2012, Santana was loaned out to newly promoted
Torino F.C. for the 2012–2013 Serie A campaign.
Genoa, later years and return to Palermo On 19 July 2013, Santana completed a move from
Napoli to
Genoa. In the January 2014 transfer window, he left Italy after 12 years competing in Serie A, signing a loan deal with
Olhanense in Portugal. He left Frosinone in January 2016 to sign a permanent deal with
Lega Pro club
Pro Patria, staying at the club also after the club's relegation to
Serie D the following season. On 22 June 2018, after Pro Patria won the Serie D title, he signed a contract extension until 2019. He left Pro Patria by the end of the 2018–19 season. In August 2019, he became the first signing of the refounded
Palermo, who will restart from Serie D, thus marking his return with the
Rosanero after thirteen years. He was also named team captain for the club's
2019–20 season. On 27 September 2020, following his appearance in Palermo's first game of the
2020–21 Serie C season against
Teramo, Santana became the first player in the club's history to have played in four different leagues (from Serie A to Serie D). A month later, he was sidelined after having contracted
COVID-19. On 3 March 2021, he scored the winning goal in a 1–0 away win at
Catania in the
Sicilian derby, which also was his first goal of the season; with this goal, he also became the first player to have ever scored at least one goal in the top four Italian divisions for Palermo. On 14 July 2023, after two years in a coaching capacity at Palermo, Santana returned to active football as a player for
Eccellenza Sicily club Athletic Club Palermo. He left the club just four months later, after appearing sparingly with the first team. In January 2024, he switched to
futsal, joining Serie A2 team Palermo C5. ==Coaching career==