Manchester United
Nani was sold to Manchester United for €25.5 million, five percent of which was paid to Real Massamá, his first professional club. He passed his medical on 6 June 2007, and signed a five-year contract one month later, joining Portuguese compatriot Cristiano Ronaldo, with whom he lived at the start of his Manchester United career.
Nani scored on his debut in a pre-season friendly against Shenzhen, scoring the third in a 6–0 win. He also scored in the following match against Guangzhou Pharmaceutical with a chip off the right post from the left side of the penalty area in a 3–0 win. On 5 August 2007, Nani made his competitive debut for United, coming on as a substitute in the Community Shield against Chelsea. He marked his debut with a trophy after they won 3–0 on penalties, following a 1–1 draw during normal time. This was followed up by Nani's third goal for the club three days later, when he scored against Glentoran in another 3–0 pre-season win.
Nani's Premier League debut came in United's opening match at home to Reading on 12 August as a substitute for Wayne Rooney, who had suffered a foot injury. Two weeks later, on 26 August, Nani scored his first competitive goal for United, netting a 30-yard goal in the 69th minute against Tottenham Hotspur. Nani also set up crucial goals for Louis Saha and Nemanja Vidić, allowing United to defeat both Sunderland and Everton 1–0, respectively. He returned to face his previous club, Sporting CP, in a Champions League tie in September, though it was teammate and fellow former Sporting player Cristiano Ronaldo who scored the winner in a 0–1 victory. Nani opened the scoring in a 4–1 home victory over Middlesbrough on 27 October.
On 16 February 2008, Nani put in a man of the match performance against Arsenal in the FA Cup Fourth Round, his goal and two assists helping United to a 4–0 win over their rivals. During the match, Nani was involved in an altercation with Arsenal captain William Gallas. After the match, Arsenal manager Arsène Wenger was equally displeased, while Gilberto Silva said Nani had a "big head".
On 23 March, Nani set up the second and scored the final goal in a 3–0 victory over rivals Liverpool, in the 79th and 81st minutes respectively, after coming onto the pitch as a substitute. On 3 May, towards the end of a 4–1 home win over West Ham United, Nani was sent off for the first time in his United career for a headbutt on West Ham defender Lucas Neill. On 21 May, Nani came on as a substitute for Wayne Rooney in the 2008 UEFA Champions League Final as United defeated Chelsea 6–5 on penalties following a 1–1 draw after extra time. 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. On 18 October, he scored from a Wayne Rooney assist to complete the 4–0 rout of West Bromwich Albion at Old Trafford. On 20 January 2009, he opened the scoring for United in their 4–2 win at home to Derby County in the second leg of their League Cup semi-final.
After Cristiano Ronaldo's transfer to Real Madrid in the 2009 close season, the weight of expectation was on Nani to step up from bit part player and replace his compatriot. 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. He recovered in time to play 17 minutes for Portugal against Liechtenstein on 12 August, however, and started the match against Birmingham City on 16 August. Although he provided the assist for Wayne Rooney's winning goal in the 34th minute, Nani was replaced by Ryan Giggs at half-time. On 22 August, Nani scored his first league goal of the 2009–10 season, a free-kick against Wigan Athletic in a 0–5 away win.
Following several poor performances, Nani criticised Sir Alex Ferguson for his lack of confidence in him. Despite this outburst, Nani was given a chance to shine and provided an assist for Rooney in the 4–0 league win over Hull City. 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. On 31 January 2010, Nani scored the first goal and set up Rooney's 100th career Premier League strike in a 1–3 league victory over Arsenal at the Emirates Stadium. Nani's goal was first thought of as a Manuel Almunia own goal by many sources, but was confirmed as belonging to Nani on 26 March by the Dubious Goals Panel. Following this performance, Nani then set up the second of a 5–0 home win over Portsmouth.
However, just four days later, he was sent off for a lunge at Stiliyan Petrov against Aston Villa, which resulted in a three-match ban and ruled him out of the League Cup final. On 10 March, Nani set up Rooney's second in a 4–0 win over Milan, before providing another assist for Rooney four days later, in the 3–0 league victory over Fulham.
On 26 March, Nani signed a new four-year contract with United, committing himself until 2014. 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. On 7 April, Nani scored his first ever European goals for United, netting two strikes in a 3–2 victory over Bayern Munich. Despite United winning the match, they were eliminated from the competition due to the away goals rule when the aggregate score was 4–4. On 24 April, Nani scored his first league goal at Old Trafford in 18 months, netting United's second in a 3–1 home victory over Tottenham Hotspur. On 2 May, Nani scored for the second match in a row, netting the only goal in a 0–1 away victory over Sunderland. Nani's third season with Manchester United ended with 34 appearances and seven goals in all competitions.
On 22 August 2010, Nani missed a penalty in the 87th minute away to Fulham, and they then equalised two minutes later through Brede Hangeland to end the match 2–2. Six days later, in a 3–0 home victory over West Ham United, Nani scored his first goal of the season and assisted Dimitar Berbatov in a Man of the Match display. Nani scored and assisted Michael Owen in a 2–2 away draw away to Bolton Wanderers on 26 September. On 16 October, Nani scored United's second in a 2–2 home draw against West Bromwich Albion. Four days later, Nani scored his first Champions League goal of the season, scoring the solitary strike in a 1–0 home victory over Bursaspor.
On 30 October, Nani scored a controversial second goal as United beat Tottenham Hotspur 2–0 at home. He scored into an empty net after Tottenham goalkeeper Heurelho Gomes rolled the ball out to take a free-kick he thought had been given for handball; however, play was allowed to go on as referee Mark Clattenburg did not blow his whistle. On 27 November, Nani scored United's fifth goal in a 7–1 home win over Blackburn Rovers. Nani netted his first goal of 2011 as he scored the winning strike in a 2–1 home victory over Stoke City on 4 January.
On 22 January, Nani scored the final goal of a 5–0 home victory over Birmingham City. Nani scored United's only goal in their first league loss of the season, a 2–1 defeat at Wolverhampton Wanderers on 5 February. Seven days later Nani scored his first Manchester derby goal, opening the scoring in a 2–1 home victory over Manchester City.
On 6 March, during United's 3–1 loss against Liverpool at Anfield, Nani was injured following a challenge from Jamie Carragher just before half-time. Nani shed tears after the challenge and was subsequently taken off the pitch in a stretcher. Following post-match comments to the press from Manchester United, it was believed Nani had suffered a broken leg. However, this was not the case as he started training the following week. It was thought Nani would miss up to three weeks as a result of this tackle and would return in April, but he recovered in time to play 61 minutes of a 2–1 victory over Marseille on 15 March.
Nani was revealed as a contender for the Professional Footballers' Association (PFA) Young Player of the Year award alongside teammate Javier Hernández on 8 April. However, many people, including Nani, expressed their surprise he was not nominated for the main award. Following this nomination, he assisted both goals in a 2–0 home win over Fulham on 9 April. Nani lost out to Jack Wilshere for the PFA Young Player of the Year award on 18 April but he was included in the PFA Premier League Team of the Year for the first time. He was awarded for his outstanding season as he was voted Players' Player of the Year at the club's awards night on 18 May.
Nani began the new season by putting in a man of the match performance and scoring twice against derby rivals Manchester City in the 2011 Community Shield, including a 94th-minute winner, as United came from two goals down to win 3–2 on 7 August 2011. He scored his first league goal of the 2011–12 season by netting United's fifth goal in an 8–2 victory over Arsenal on 28 August. Nani made his 100th Premier League appearance on 18 September as he scored in a 3–1 home win over Chelsea. He scored with a long-range strike after cutting inside from the right wing. He was also awarded the man of the match. In United's following league match at the Britannia Stadium, Nani scored his third goal of the season in a 1–1 draw with Stoke City. He played a neat one-two with Darren Fletcher before making his way through Stoke's defence and firing a low shot inside the left post. Nani started the match against Manchester City, where they fell victim to a 1–6 beating at home to their neighbours. On 1 November, Nani was shortlisted for the prestigious FIFA Ballon d'Or.
On 10 December, the first match after United's elimination from the UEFA Champions League, Nani scored a brace in a home match against Wolverhampton Wanderers. He opened the scoring in the 17th minute to put them 1–0 up with a shot into the bottom left corner. He scored his second goal in the 56th minute, tapping in from Antonio Valencia's drilled cross across the six-yard box to extend the lead to 3–1. He was later replaced by winger Ashley Young as the match finished 4–1 to the home side. Nani scored his sixth league goal of the season and provided two assists in a 5–0 away win at Fulham on 21 December. He first advanced on a run down the left flank before crossing for Danny Welbeck to slot home. He then met a Ryan Giggs cross with his head to glance United into a 2–0 lead. He then returned the compliment, squaring for Giggs to put United 3–0 up before half-time.
During Manchester United's 2–1 win against Arsenal on 22 January, Nani sustained a foot injury from a tackle by Arsenal defender Laurent Koscielny in the 75th minute and was replaced by Ashley Young. After a scan on Nani's foot, he was feared to have suffered a metatarsal injury, thus not being able to play for two months. Nani returned to football on 15 April at United's match against Aston Villa as a substitute, replacing Young on the left wing. He scored a goal in stoppage time (93rd minute) with a low shot past Villa goalkeeper Shay Given from Jonny Evans' through-ball assist, resulting in a 4–0 win over Villa. Nani then followed this with another goal when chipping Tim Howard at his near post in a 4–4 draw at Old Trafford against Everton.
During the season Nani scored a single Premier League goal, and three in all competitions, marking a significant decrease compared with previous seasons. He played just 11 times in the league, including only seven as a starter, although United ended up winning the league 11 points ahead of second place, to give Nani his fourth Premier League winner's medal. His most memorable appearance in the season came in the second leg of United's UEFA Champions League round of 16 tie with Real Madrid. With Manchester United leading 1—0, Nani was sent off in the 56th minute for a high boot on Álvaro Arbeloa; Real Madrid took advantage of their numerical superiority and scored twice to win the match 2–1, and the tie 3–2 on aggregate.
On 5 September 2013, Nani renewed his contract with Manchester United, which was to keep him at the club until 2018. He started his first match of 2013–14 season against Liverpool in the League Cup. Despite this, Nani spent most of the season struggling against injury and trying to find form. He scored only once during the season.
On 19 August 2014, Sporting CP announced the return of Nani to the club on a season-long loan from Manchester United, as part of a deal that brought centre-back Marcos Rojo to United. Nani was given the number 77 shirt.
Nani made his comeback at the Estádio José Alvalade in a Primeira Liga match against Arouca, four days after signing. He missed a penalty, received a yellow card and was substituted in the 77th minute as the match ended in a 1–0 win for Sporting. He scored his first goal of this loan on 17 September, opening a 1–1 draw at Maribor in the first match of the 2014–15 UEFA Champions League group stage. He was also voted Man of the Match. Nani scored his first league goal for the club four days later in a 4–0 win against Gil Vicente On 3 January 2015, Nani was sent off for two bookings in a 3–0 win over Estoril. Nani scored in Sporting's penalty shootout victory over Braga in the 2015 Taça de Portugal final, which earned the club their first trophy since 2008.
