At the end of the season, Quaresma was given the Bidone d'oro award for the worst footballer in the Italian top division. On 2 February 2009, transfer deadline day, he signed on loan for Premier League club Chelsea until 30 June, making his first appearance five days later in a 0–0 home draw to Hull City. On 7 March, he provided the cross for Alex to score against Coventry City in the sixth round of the FA Cup; after a disappointing start at the San Siro, the player claimed his move to Stamford Bridge had restored his confidence, and he further declared "When I was at Inter, I wasn't feeling very confident. I wasn't playing well and wasn't happy, I already feel more confident here at Chelsea. It has brought the joy back for me, which I didn't have at Inter."