Webster did not drop a set in seeing off Mick McGowan and Terry Jenkins at the 2016 World Championship, but then lost 4–1 to Alan Norris in the third round. Two semi-finals and a quarter-final in the UK Open Qualifiers saw him finish fifth on the Order of Merit to enter the UK Open at the third round stage. He defeated Matthew Edgar 9–3, Dirk van Duijvenbode 9–4 and Mensur Suljović 9–5 to reach his third major quarter-final in six months and was comfortably beaten 10–3 by Phil Taylor. Webster and Gerwyn Price lost 4–2 in a doubles match in the second round of the World Cup. After his 10–6 defeat to Adrian Lewis in the opening round of the World Matchplay, Webster said that dartitis, which he has fought over the past few years, was evident in the latter half of the game and that he was trying to beat the player and himself during matches. He reached one Pro Tour quarter-final during the rest of the year as well as losing in the first round of the Players Championship Finals.