Career
Aldershot Town
Born in Aldershot, Hampshire, Winfield came through the ranks of the Aldershot Town youth team and was loaned out to Isthmian League Division Two side Chertsey Town in the 2004-2005 season. He signed a one-year professional contract with Aldershot on 16 July 2005 and joined Isthmian League Premier Division club Staines Town on loan in early 2006. Winfield made his debut in a 3–1 home defeat to Wealdstone on 2 February 2006 and had made seven appearances when returning to Aldershot in March.
Unfortunately, a knee injury sustained in the Conference League Cup final against Rushden & Diamonds resulted in him missing pre-season training ahead of the Shots" first season in League Two.
Having begun training at the end of 2008, Winfield was loaned out to Salisbury City of the Conference Premier in January 2009 on a one-month deal that saw Andy Sandell move the other way on a permanent deal. Winfield made his Football League debut in Aldershot"s 1–2 defeat to Exeter City in February 2009.
Wycombe Wanderers
Winfield signed a two-year deal for Wycombe Wanderers upon the expiry of his contract in June 2010, and a tribunal ruled that Wycombe pay a fee of £25,000 plus a 20% sell-on clause. Shrewsbury Town
Winfield turned down a new contract at Wycombe at the end of the 2012-2013 season, to join League One side Shrewsbury Town on a free transfer on 12 June 2013.
However he picked up a hamstring injury late in pre-season that delayed his availability for selection until September 2013.
Having played 30 minutes of a reserve match against Oldham Athletic, Winfield eventually made the substitutes" bench for an away match at Crawley Town on 14 September 2013, and made his first team debut away at Bradford City two weeks later, getting sent off for two bookable offences in a 2–1 defeat. Following Shrewsbury"s relegation from to League Two, Winfield was released on 2 June 2014, having come to an agreement to end his contract early. York City
Following his release from Shrewsbury, Winfield joined League Two rivals York City on a two-year contract on 16 June 2014.
He made his debut in a 1–0 home defeat to Doncaster Rovers in the League Cup first round on 12 August 2014.
Winfield made only five appearances for York before joining their League Two rivals AFC Wimbledon on a one-month loan on 12 February 2015. He made his debut two days later in a 2–0 away defeat to Shrewsbury before the loan was extended in March 2015.
He had made seven appearances for AFC Wimbledon when York recalled him on 19 March 2015 after an injury to Stéphane Zubar.
