The 36-year-old centre-back has a wealth of experience under his belt both in the EFL and National League having started his career at Aldershot Town where he worked his way through the ranks.
He won promotion to League Two by lifting the Conference title with the Shots in 2008 before moving on to Wycombe Wanderers in 2010.
A three-year stay with the Chairboys saw him celebrate a second career promotion in 2011 as Wycombe secured a place in League One.
After making 100 appearances in a three-year stay at Adams Park, Winfield moved on to Shrewsbury Town for the 2013/14 campaign, before joining York City in 2014.
His two-year stay at York saw him play 51 times whilst taking in a short loan spell with AFC Wimbledon, before moving back into non-League football with Ebbsfleet United in 2016.
A successful three years at Stonebridge Road saw Winfield score a vital goal in the National League South play-off final victory over Chelmsford City in 2017. He eventually became a Chelmsford player for a stint in 2019, signed by then Clarets boss Rod Stringer, before stepping back up to the National League with Bromley midway through the 2019/20 campaign.
His career then briefly took him to Romford in 2020 before he made a return to Chelmsford in 2021 where he would remain as a mainstay in their defence for a further three seasons.
He now rejoins Stringer as he continues to build his Wings squad for the 2024/25 season.