Webster saw off John Henderson 3–1 in the opening round of the 2016 World Championship, but Michael van Gerwen averaged 109.23 in their second round clash as Webster could only win one leg in a 4–0 defeat. A 9–8 win over Ricky Evans saw him reach the fifth round of the UK Open for the second time in his career and he lost 9–5 to Peter Wright. Webster's first semi-final in over two and a half years came at the ninth Players Championship and he was beaten 6–1 by Benito van de Pas. Another came at the 17th event, but he was whitewashed 6–0 by Van Gerwen. Webster was already eliminated from the Grand Slam of Darts before his third group game with Phil Taylor after losing his opening two matches, but nevertheless thrashed the 16-time world champion 5–0. Webster stated that the result would give him a confidence boost for the remainder of the year. He was right, because at the Players Championship Finals he saw off Jonny Clayton and Simon Whitlock both 6–3, Alan Norris 10–5 and Christian Kist 10–6 to reach the semi-finals of a PDC major for the first time. Webster stormed in to a 6–0 lead over Van Gerwen, but missed a dart to be 7–2 ahead as Van Gerwen closed to 6–6. Webster did take a one leg lead on two further occasions, but would ultimately be defeated 11–8.