Career
Wolverhampton Wanderers
Winnall joined the youth ranks of Wolverhampton Wanderers as a teenager, before signing professional forms in May 2009. He recovered from a cruciate knee injury to make his senior debut on 24 August 2010 in a League Cup victory over Southend United, which was to be his only Wolves first team appearance. In February 2011 he moved on a month"s loan to League Two side Burton Albion, later extended to the end of the season after a run of four goals in six appearances.
The striker went out on loan again, joining League Two side Hereford United on a month"s loan from 26 August.
After returning to Wolves at its conclusion, he moved on loan again in January 2012, to join Scottish Premier League side Inverness Caledonian Thistle for the rest of the season. During pre-season for the 2012-2013 season Winnall was given permission to undergo a trial with Preston North End but was not offered a contract.
Instead his next move was a loan at League One club Shrewsbury Town whom he joined in a one-month deal on 28 September 2012. At the end of the 2012-2013 season his contract with Wolves expired and was not renewed, meaning the striker left the club having made only one first team appearance during his time at Molineux.
Scunthorpe United
Following a successful trial spell during pre-season, he subsequently signed for League Two club Scunthorpe United in a one-year deal, scoring on his debut on 3 August 2013 against Mansfield Town.
Scunthorpe took up a one-year option on his contract in May 2014, extending his deal until 2015. At the same time, Winnall was offered a new contract which – according to Scunthorpe chairman Peter Swann – was a "vast improvement" on his current deal. Swann said: "lieutenant"s important that the fans know that we do rate him and that we want him to stay here."
Barnsley
On 23 July 2014, Winnall signed for fellow League One club Barnsley for an undisclosed fee.
On 28 January 2016, Barnsley rejected an offer for Winnall from Championship club Leeds United.