In 2014, Kirk reached the last 64 in two of the six UK Open qualifiers to enter the event in the first round stage. He beat Conan Whitehead 5–4 and Gerwyn Price 5–2 to face 16-time world champion Phil Taylor in the third round. In Kirk's first televised match he caused one of the biggest shocks in the history of darts by winning 9–7. He then played Peter Wright, who had been the World Championship runner-up at the beginning of the year, and continued his amazing run by taking out two ton-plus finishes and coming back from 5–3 down to triumph 9–5. In the fifth round Kirk and Brendan Dolan shared the first 14 legs, before the Northern Irishman won the match with two 13 dart legs. Kirk earned £5,000 for his run in the tournament, by far the biggest of his career to date. In July, Kirk reached the final of the 12th Challenge Tour event of the year where he was edged out 5–4 by Brett Claydon.