Woolford started his career in the Northern Counties East Football League Premier Division with Glasshoughton Welfare after progressing through their youth system.

[6] He comes from a family of professional sportsmen; father Neil and grandfather Cyril were both rugby league players with Featherstone Rovers.

[9] Woolford started his career with Northern Counties East Football League Premier Division team Glasshoughton Welfare in 2002 after progressing through their youth system.

[12][13] He played one match for the youth team of Doncaster Rovers in April 2005,[14] but was not taken on by the club, and was also rejected by Barnsley and Bradford City.

[21] He eventually signed for Conference National club York on 31 August for an undisclosed five-figure fee after having made four appearances and scored one goal for Frickley at that point in 2006–07.

[28] He featured in both legs of York's play-off semi-final defeat by Morecambe 2–1 on aggregate and finished 2006–07 with 45 appearances and eight goals,[29] after which the club exercised their option to extend his contract for another season.

[34] Manager Colin Walker confirmed that several enquiries had been made about signing Woolford during the January transfer window.

[36] He was watched by Crewe Alexandra's director of football Dario Gradi in April 2008,[37] after which Walker insisted he was still a part of York's plans for the next season.

[44] He scored four minutes into his first start for Scunthorpe against Brighton & Hove Albion on 6 September 2008, giving his team the lead, in a match which eventually finished 4–1.

[51] Woolford signed a three-and-a-half-year contract with fellow Championship club Bristol City after joining for an undisclosed fee on 31 January 2011.

[56][57] Woolford signed a two-year contract with League One club Sheffield United on 14 July 2015, having previously played under manager Nigel Adkins at Scunthorpe.

[58] He was released by United on 19 August 2016, having fallen out of favour under manager Chris Wilder,[59] and immediately joined League One club Fleetwood Town on a one-year contract.

[61] On 31 August 2017, Woolford signed a one-year contract with League Two club Grimsby Town on a free transfer.

[70] His debut came in a 1–1 draw with Grenada on 31 May 2008 and was described as a "constant threat down the left",[71] and earned his second cap as a 67th-minute substitute against Barbados on 2 June.

[78] He achieved a Higher National Diploma in civil engineering and has said he is looking to complete this degree before the end of his football career.