Wesolowski lost his place in the first team the following season, playing just four cup matches. On 2 October 2008, he joined Cheltenham Town on a three-month loan deal, linking up with former Leicester manager Martin Allen and fellow loanee Barry Hayles, with the option of being recalled after the first month. His loan ended early after suffering a fractured ankle in a 2–0 away defeat to Tranmere Rovers in October. On 2 February 2009, Wesolowski joined Dundee United on loan for the remainder of the 2008–09 season, with the option of making the deal permanent. He made his debut in a 1–0 home defeat to Hearts, playing for 65 minutes before being substituted.