Wesolowski played for Australian side Northern Spirit before signing for Leicester City in 2002. 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. He underwent surgery on the leg but the injury sidelined him until the start of 2006. Wesolowski returned and impressed for the Leicester first team, making his debut at home to Cardiff City in January 2006. However, after only five appearances, he broke his same leg against Brighton in February. He recovered in time for the start of the 2006–07 season, although a thigh injury kept him out of the side for the first month. 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. He scored his first senior goal in a 4–3 FA Cup defeat to Fulham on 17 January 2007. Wesolowski played a total of 19 league games, helping Leicester survive relegation. In July 2007, Wesolowski agreed to a contract extension with Leicester that would see him remain at the club until 2011. He scored his second goal of his career in a 1–0 League Cup win over Accrington Stanley on 14 August 2007, before being sidelined for six weeks with a hamstring injury on 18 September in a 3–2 League Cup win over Nottingham Forest. Wesolowski had more hamstring problems following recovery, and he was injured again on 8 December in a 2–1 defeat to West Brom, sidelining him until Christmas. Despite playing a total of 22 league games, Wesolowski could not prevent Leicester from being relegated at the end of the 2007–08 season. 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. After featuring in every match since arriving, Wesolowski suffered a hamstring injury in early May in a match against Hibernian, ending his season. On 4 August 2009, Wesolowski joined SPL side Hamilton Academical on loan for an initial six-month period, which was extended till the end of the season after some impressive run of form.
On 8 August 2011, Wesolowski signed a one-year deal with league one club Oldham Athletic. On 22 October 2011, Wesolowski scored his first goal for the Latics. He scored the opener in a 2–0 win against Wycombe Wanderers. Wesolowski had his best season for the club yet in the 2013–14 season, he played nearly every game for the club & scored 5 goals, his best ever goal – scoring season. The vast improvement he had shown resulted in him scooping up 5 awards at the end of season awards, including Player of the Year. On Wednesday 7 May, when the clubs retained list was announced, it was confirmed that a formal contract offer had been made to Wesolowski. With Wesolowski stating that he "would love to stay here" and that he would like to come to an arrangement with the club over a new contract.
On 6 June 2014, despite a contract offer from Oldham, Wesolowski moved to Shrewsbury Town in League Two on a free transfer. He made his debut on the opening day of the season, coming on as a substitute in a 2–2 draw away at A.F.C. Wimbledon, and was a regular in the first team squad until suffering a season-ending injury in a home match against Hartlepool United on 17 January 2015 where he ruptured two knee ligaments. He scored his first and what turned out to be only goal for Shrewsbury in a 2–1 win over Portsmouth on 25 October 2014. 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. After playing a full ninety minutes and scoring Shrewsbury's equalising goal in their Shropshire Senior Cup final win against local rivals AFC Telford United, he returned to the first team ahead of schedule in a home match against Sheffield United in April 2016. At the end of the season, Wesolowski was offered a new contract – reportedly on reduced terms – and was still training with the first-team during the following pre-season. He was later reported to be training with National League side Lincoln City, but was unable to agree to a contract.
Guiseley
Wesolowski joined National League club Guiseley in October 2016.
Football League Two runner-up, second-place promotion: 2014–15
Country
;Australia
OFC U-20 Championship: 2005
Individual
Oldham Athletic Player of the Year: 2013–14
International career
Wesolowski was born in Australia, and is of Polish descent through his grandfather. 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. 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'. On 6 November 2007, he was called up to the national team for a friendly match against Nigeria on 17 November, but was an unused substitute as Australia won 1–0.