Career
He is his nation"s most-capped player of all time, having played all 17 of their matches. Chipolina began his career with Linense of the Spanish Segunda División B and Tercera División, the third and fourth tier of the Spanish football league system respectively, between 2007 and 2012. In 2011-2012, Chipolina played one season at Civil Defense San Roque of the Tercera División.
In March 2012, Chipolina earned a week-long trial at Leyton Orient of England"s League One.
Chipolina and San Roque terminated his contract by mutual consent in April 2012. In total, Chipolina made 26 appearances for the club
On 2 July 2014, Chipolina scored the first goal for a Gibraltarian club in the Union of European Football Associations Champions League, with a penalty to give Lincoln Red Imps the lead over HB Tórshavn of the Faroe Islands in a 1–1 draw. Between 2007 and 2013, Chipolina appeared in seven matches for Gibraltar and scored five goals before Gibraltar applied for and was granted Union of European Football Associations membership.
One of his caps came in a friendly match against England C which garnered interest in the player from Leyton Orient and Scotland"s Livingston.
He was also a part of the squad that competed in the 2011 Island Games. Chipolina made history by being the first Gibraltarian player to score in an official Union of European Football Associations match when he scored for the Gibraltar national futsal team in a Union of European Football Associations Futsal Championship match against Montenegro in 2013. Chipolina made his international debut in the match, a start in the eventual 0–0 draw.
Chipolina works as an admin clerk in Gibraltar.