In December 2013, Webster lost to James Wade in the first round of the 2014 World Championship, despite leading 2 sets to 1 (first to 3). He missed six darts to win the match, to which Wade responded in three straight legs, thus winning the match. He played in the World Matchplay for the first time since 2005 and was beaten 10–4 by Taylor in the first round. Webster's resurgence of form also saw him play in his first World Grand Prix and Grand Slam of Darts, but he lost in the opening round of the former and was defeated in all three of his group games in the latter. A final appearance in a major event of the year came at the Players Championship Finals where he missed two match darts in the deciding leg of the first round against Robert Thornton to lose 6–5.