Silva scored his first career goal in a 2009–10 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. On 28 November 2009, in the Lisbon derby, which ended 0–0, he made headlines in the Portuguese media because he covered the most distance of any Sporting player, having traveled over . Coach Carlos Carvalhal started him in 13 of the team's next 15 matches, but he eventually fell out of favour, as Sporting went on to finish in only fourth place with 48 points, the club's worst points total since the 1992–93 campaign.