O'Connor entered 2014 ranked world number 68, just outside the top 64 who had full playing privileges for the year ahead. He entered Q School and had his best result on the third day when he was defeated 5–0 by Pete Dyos in the last 16. The result helped him finish 24th on the Q School Order of Merit to claim the final place on offer for a two-year tour card. He was edged out in the third round of the UK Open 9–8 by Jamie Lewis. O'Connor and Finnan lost five successive legs in the first round of the World Cup of Darts to be beaten 5–3 by Singapore. He was knocked out in the first round of two European Tour events, before picking up his first victory of the season at the European Darts Trophy by averaging 104.36 in a 6–4 win over Mensur Suljović. In the second round, O'Connor was 5–4 ahead of Justin Pipe but bust his score when on 70 and missed one match dart at double six to be beaten 6–5.