After showing a lot of potential in the reserves, Wesolowski played for Leicester in a pre-season friendly against Celtic in 2005, but suffered a broken leg due to a challenge from Bobo Baldé.

[3] The departure of Joey Guðjónsson gave Wesolowski the opportunity to become a first team regular, although he still faced stiff competition from then-teammates Stephen Hughes and Andy Johnson for the central midfield spot.

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.

[13] On 4 August 2009, Wesolowski joined SPL side Hamilton Academical on loan for an initial six-month period,[14] which was extended till the end of the season after some impressive run of form.

[24] Wesolowski returned to the side following their promotion to League One, but suffered a further knee injury in September 2015 just three matches into his comeback, which was initially thought to rule him out for the rest of the season.

[31] Wesolowski received international acclaim at the end of the 2004–05 season after competing for Australia in the FIFA World Youth Championship and was labelled "a star in the making" by the Australian Football Federation.

[32] Wesolowski was called up to the Australian national team on his 19th birthday for the 2007 Asian Cup qualifier against Kuwait, but was withdrawn from the squad days later after consultation with medical staff from both parties 'on precautionary grounds'.