He then defeated Robbie Green 4–1 in the second, Stephen Bunting 5–1 in the quarter-final and Jan Dekker 6–2 in the semi-finals, thus making him one of a small number of players to have reached the final at his first attempt.
[8] Winstanley's results during his first 6 months on the tour were good enough to seal a place in the World Matchplay due to his ranking on the ProTour Order of Merit.
[11] His doubles continued to prove a weakness in his game as he missed two for the match in a 2–3 loss to Dave Chisnall in his debut performance in the World Grand Prix.
[12] Winstanley went into the last round of matches at the Grand Slam of Darts knowing a win over Simon Whitlock would secure his place in the knockout stages.
He produced a superb performance to win 5–1 with a 100.63 average, before seeing off Arron Monk 10–5 and Kevin Painter 16–12 to reach his first PDC major semi-final.
[16] The week before the tournament Winstanley practised intensely with five-time world champion Raymond van Barneveld, playing two four- to six-hour sessions a day at the Ducthman's home with the players aiming to take out 5001 in 50 turns.
[23] He qualified for the 2014 World Championship through the 2013 ProTour Order of Merit and fell 2–0 down to Richie Burnett in the first round, before missing one dart to square the match at two sets all and was instead beaten 3–1.
[26] He enjoyed a good run at the UK Open by beating Andy Boulton 9–2 and reigning BDO world champion Stephen Bunting 9–6, before losing to Kevin Painter 9–5 in the fifth round.
[30] A first round exit at the European Championship followed and Winstanley was knocked out of the Grand Slam in the group stage after failing to win any of his three games.
[31] However, he found his form at the Players Championship Finals by averaging 103.94 in a 6–3 triumph over Simon Whitlock and then beat Jelle Klaasen 10–5 to play in his first major PDC quarter-final.
[33] Winstanley secured narrow 3–2 and 4–3 wins over Wayne Jones and Darren Webster in the 2015 World Championship to reach the third round of the event for the first time.
[40] On 15 November 2016, Winstanley was fined £3,000 and suspended from the PDC until May 2017 for posting a live recording of an event showing inappropriate behaviour.