[8] At the age of 15 he was scouted by Chelsea, along with Portugal under-16 teammates Ricardo Fernandes and Fábio Ferreira, and the three players trained at the English club's facilities in January 2005.

[5] In July, after spending the final two months of the season playing with the reserve team, he was officially promoted to the main squad by manager Paulo Bento ahead of the upcoming campaign.

[5] He made his Primeira Liga debut on 17 August, taking the field as a late substitute in a 4–1 home win against Académica de Coimbra;[11] on 12 December, after appearing as an unused substitute in several league and European matches, he made his first professional start and Champions League debut in a 3–0 victory over FC Dynamo Kyiv.

[21] Silva scored his first career goal in a UEFA Europa League group stage match against Hertha BSC, the match-winner in a 1–0 win, when he also was sent off after collecting a second yellow card in injury time.

[22] On 28 November 2009, in the Lisbon derby, which ended 0–0,[23] he made headlines in the Portuguese media because he covered the most distance of any Sporting player, having traveled over 10,049 metres (6.244 mi).

[37] He scored a career-best ten competitive goals in the 2014–15 season, while also helping the team reach and win the final of the Portuguese Cup.

[41] After the move was finally completed, he returned to Lisbon on 1 October 2017 and wished his former fans an emotional farewell before the 0–0 draw with FC Porto.

[46] Silva was officially registered on 1 January 2018, and made his debut that same day as a late substitute in a 3–0 win at home to Huddersfield Town in the Premier League.

[48] In a 2–0 defeat of Watford on 20 January, he came on for Jamie Vardy in the 89th minute and provided the assist for Riyad Mahrez's goal in stoppage time.

[52] On 31 January 2019, Silva joined AS Monaco FC – coached by his compatriot Leonardo Jardim – on loan until June, with Youri Tielemans moving in the opposite direction.

[53][54] He made his Ligue 1 debut on 2 February, playing 18 minutes in the 2–1 home victory over Toulouse FC after replacing fellow Portuguese Gelson Martins.

With the under-16s he appeared at the Tournoi du Val-de-Marne, featuring in all three group stage matches – however, after he was found to have done unauthorised training with Chelsea, he was suspended by the Portuguese Football Federation.

[5] He played with the under-17 team as they attempted to qualify for the 2007 UEFA European Championship, being a regular as the side eventually fell short in the elite round.

He scored his first goal in the age group on 6 November 2007, in the first round of qualification for the 2008 European Championship against the Republic of Ireland;[69] despite a 2–1 victory, Portugal failed to progress past the elite stages.

On 5 February 2009, Silva earned his first call up to the under-21 team under coach Rui Caçador, for a friendly match with Switzerland that was played five days later.

He made his senior international debut in another friendly, replacing André Gomes midway through the second half of a 1–0 win over Argentina at Old Trafford on 18 November.

[75] His first game in the tournament took place on 25 June, when he played the full 120 minutes in the round of 16 clash against Croatia, a 1–0 win after extra time.