He recovered from a cruciate knee injury[4] to make his senior debut on 24 August 2010 in a League Cup victory over Southend United,[5] 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,[6] later extended to the end of the season after a run of four goals in six appearances.
[8] 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.
[11] At the end of the 2012–13 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.
[12] Following a successful trial spell during pre-season, he subsequently signed for League Two club Scunthorpe United in a one-year deal,[13] scoring on his debut on 3 August 2013 against Mansfield Town.
[20] On 14 May 2016, Winnall's double helped keep Barnsley on course for a return trip to Wembley as a 3–0 first-leg win against Walsall gave them a big advantage in their League One play-off semi-finals.