He also got his first taste of first team football in December 2007, when he was named as an unused substitute for United's dead rubber Champions League group stage match against Roma.

[8] Eckersley made his Burnley debut in the 2009–10 Football League Cup, playing in the club's second round match against Hartlepool United.

[9] On 5 March 2010, Eckersley joined Plymouth Argyle on a one-month loan deal as cover for the injured Réda Johnson.

[10][11] The move also allowed Eckersley much-needed match experience, having made just three cup appearances for Burnley since joining from Manchester United.

[21] Eckersley made his debut for Toronto on 23 April 2011 in a 1–1 home draw against Columbus Crew as a second half sub for Javier Martina.

On 25 January 2012, Burnley announced the cancellation of Eckersley's contract by mutual consent, allowing him to make a permanent move to Toronto FC.

[26] Eckersley then provided an assist for Ryan Johnson to score the only goal for Toronto, as they lost 2–1 against Sporting Kansas City.

[27] For the second time running, Eckersley established himself in the right–back position,[28] though played in the centre–back with Darren O'Dea[29] and helped Toronto to another Canadian Championship later that season.

[34] On 27 January 2014, Toronto FC traded Eckersley to New York Red Bulls in exchange for a fourth-round pick in the 2017 MLS SuperDraft.

[35] Eckersley made his New York Red Bulls debut in the opening game of the season, in a 4–1 loss against Vancouver Whitecaps on 9 March 2014.

Eckersley finished the season very strong playing an important role in the team getting to the eastern conference final.

[39] After leaving New York Red Bulls, Eckersley went on trial at La Liga side Elche[40] and Southend United, but didn't get a contract.