Silva joined Fluminense's youth setup in 2004, from neighbours Portuguesa. In December 2008 he was invited to a trial period at Arsenal, and scored four goals in a single match against Norwich with the Academy side. He returned to Brazil, however, and was assigned back to the youth setup at Flu. On 31 December 2009 Silva agreed a deal with Arsenal, for a £3.5 million fee. The deal was delayed until 2011 due to his age. On 28 February 2010 Silva made his senior debut for Fluminense, starting and scoring the second of a 5–1 home routing over Friburguense for the Campeonato Carioca championship; his Série A debut came on 9 May, coming on as a late substitute in a 1–0 loss at Ceará. In October, Silva was widely criticised by coach Muricy Ramalho, after his complaints due to the lack of opportunities, and subsequently appeared rarely after the disruption with his manager.
Arsenal
On 31 January 2010, Silva signed for Arsenal, and featured in a reserves match against Manchester United on 19 August 2010. He played the whole 90 minutes and scored, cutting in from the right to hit the back of the net. He played in a closed-doors friendly for Arsenal in January 2010 against Dagenham and Redbridge, scoring a brace and setting up a third, being replaced after 70 minutes. On 9 December 2010 it was announced that the FA had backtracked on its initial decision to award Silva his "Special Talent Visa". The next day, it was announced on Arsenal's official website that the club planned to send him out on loan due to the fact he couldn't get a work permit. On 30 October 2014, it was reported that Silva had obtained the necessary work permit to play for Arsenal from the start of the following season.
Loans in Spain
On 12 January 2011, Arsenal loaned Silva to La Liga side Levante UD until June. He made his debut on the 29th coming on as a late substitute in a 2–0 home success against Getafe CF. Silva only appeared again on 21 May, again from the bench in a 2–1 home loss against Real Zaragoza. On 10 July 2011, Silva rejoined the Granotes. However, after making no appearances for the Valencian side, he moved to CD Alcoyano in Segunda División on 12 January of the following year, also in a temporary deal. On 20 August 2012, Silva joined SD Ponferradina on a season-long loan. He scored his first goal for the club in a 2–0 win at Villarreal CF, for the campaign's Copa del Rey. Silva scored his first league goal for Ponfe on 11 November, but in a 5–3 home loss against Córdoba CF. He finished the season with 20 appearances as the Castile and León side narrowly missed out the play-offs. In August 2013, Silva joined Real Murcia, again on loan. He appeared in 38 matches during the campaign, as his side was eventually knocked out in the play-offs. On 16 July 2014, Silva moved to UD Almería also in a season-long loan deal. On 15 April of the following year was issued with a Spanish passport, allowing him to qualify automatically to work in the United Kingdom, and thus play for Arsenal.
On 18 August 2015, Silva joined Championship side Bolton Wanderers on a season long loan. At the time of the signing, Arsene Wenger said "He’s absolutely stunning to watch and I believe Bolton will be surprised by his quality." Silva made his debut for the club on 21 August in their 1–1 home draw against Nottingham Forest, lasting eighty four minutes before he was substituted for Emile Heskey. He scored his first goal for Bolton in a 4–3 defeat at Queens Park Rangers on 3 October 2015. Silva suffered a hamstring tear during a 1–0 defeat to Birmingham City on 20 October, causing him to miss two months of the season.
Return to Fluminense
On 18 July 2016, Wellington Silva returned to his former team Fluminense on a four-year contract. His name changed to Wellington to not be confused with Wellington Silva. In 2018, Fluminense dealt Wellington Silva to Internacional.
