Caven beat Jelle Klaasen 3–1 in the first round of the 2014 World Championship to set up a meeting with Raymond van Barneveld. Caven took the first set in a deciding leg by hitting a 136 finish with Van Barneveld waiting on 20 and then missed one dart to take a 2–0 lead, instead going on to trail 2–1. Caven won two successive sets to regain the advantage but could only win one more leg after this in a 4–3 defeat. He was the victim of a shock 5–3 defeat against Kevin Dowling in the second round of the UK Open. In May, he advanced to the semi-finals of an event for the first time in a year at the ninth Players Championship where he lost 6–2 against Peter Wright. Caven beat Terry Jenkins, Stephen Bunting, Phil Taylor and Wright all by 6–5 scorelines at the Austrian Darts Open to reach the final. He built a 5–2 lead over Vincent van der Voort, but went on to lose 6–5 without ever having a dart for the title. Caven was knocked out of the first round in the World Matchplay and World Grand Prix and the second round of the European Championship. He won a place in the Grand Slam of Darts through the qualifier but lost each of his group games to finish bottom of the table. Caven saw off Ian White 6–4 at the Players Championship Finals and was almost the victim of a huge fightback from Robert Thornton as he forced a deciding leg after having been 9–4 behind. However, he survived one match dart to win 10–9 and reach his only major quarter-final of the year where he faced Adrian Lewis. Caven missed a dart for the match at the bull to complete a 167 finish to win 10–8 and was instead eliminated 10–9.