After playing non-league football briefly, he began his professional career with spells at Stockport County and Huddersfield Town.

United of Manchester and signed initially on a short-term contract at Edgeley Park,[2] and made an instant impact on the team, scoring three goals in his first four games for the club, including two against Shrewsbury Town at Gay Meadow.

Pilkington then played a big part in County's record breaking run of results during January and February 2007.

[3] On 30 June, the club announced that Pilkington had declared his intention to leave following their failure to win promotion from League One.

[6][7] He made his first appearance since his injury in the 1–1 friendly draw versus Real Zaragoza on 3 August 2011, coming off the bench to replace Bradley Johnson.

Pilkington made his competitive Norwich debut in the opening day Premier League 1–1 draw at Wigan Athletic, replacing Steve Morison.

[16][17] With the club short on forwards following departures in the January transfer window, Pilkington was moved into an unfamiliar more advanced role playing as a striker and finished the season with nine goals in total, including braces against Rotherham United and Preston North End,[18][19] finishing the season as the club's top scorer.

[23] Despite the uncertainty of his future, Pilkington stayed at the club during the summer of 2017, making appearances in the EFL Cup and scoring against Burton Albion.

[24] He made his first league appearance on 16 December, starting in a 1–0 win over Hull City, due to the club being left without a recognised striker.

[30] On 17 October 2020, Pilkington moved to Indian Super League and signed with SC East Bengal, managed by Robbie Fowler.

[33] Pilkington left East Bengal at the end of the 2020–21 season because he had agreed terms with League One side, Fleetwood Town.

[39] Giovanni Trapattoni and Marco Tardelli were reported to have been keeping an eye on him ahead of Ireland's participation in UEFA Euro 2012.

[40] In January 2013, Pilkington was called up for the Republic of Ireland Senior Team to play Poland in a friendly in February.

[41] The Norwich winger played almost 20 minutes during Ireland's 2–1 loss to Sweden in Dublin on 6 September 2013 as a replacement for James McClean in a 2014 FIFA World Cup qualification (UEFA) game.