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At the age of nine, he began training with Sporting CP and S. Benfica on alternate days, eventually joining Sporting's youth squad after they offered him pre-season training.

Individually, Nani was included in the Professional Footballers' Association (PFA) Premier League Team of the Year on one occasion and was a nominee for the PFA Young Player of the Year in 2011.

Nani took and scored Manchester United's crucial fifth penalty in the shootout.

Nani scored his first goal of the 2008–09 season on 23 September 2008, scoring United's third goal in a 3–1 win over Middlesbrough in the last minute to secure passage to the Fourth Round of the League Cup.

Nani's first contribution to United's new season was opening the scoring in the tenth minute of the 2009 FA Community Shield, but United eventually lost the match on penalties after a 2–2 draw.

Nani suffered a dislocated shoulder during the match, which was originally expected to keep him out of the start of the season.

Soon after this positive display, he put in another good performance in their League Cup semi-final victory over derby rivals Manchester City, revealing a heart-to-heart with Ferguson had resulted in a better display of form.

A day later, Nani took his assist tally in the league for the season to nine as he set up two goals in a 0–4 win over Bolton Wanderers at the Reebok Stadium, providing goals for Dimitar Berbatov and Darron Gibson.

The Quinta da Marinha Golf Course, in Cascais, has 18 holes with 5.870 meters of pure nature and big challenges.