Dolan once again failed to produce his best form at the World Championship in the 2016 event as he was whitewashed 3–0 by Kyle Anderson in the first round. He lost 9–6 to amateur Barry Lynn in the third round of the UK Open. Dolan partnered Daryl Gurney at the World Cup for the first time and they saw off Japan, Ireland and Canada to reach the semi-finals, where they lost both their singles matches against the English pairing of Phil Taylor and Adrian Lewis. At the World Matchplay he beat Raymond van Barneveld 10–7, before losing 11–8 to Mervyn King. Before the World Grand Prix Dolan married his partner Teresa and then defeated Peter Wright 2–0 in the first round, but was then eliminated 3–1 by Dave Chisnall. Dolan recorded victories over Max Hopp and Martin Adams to qualify from his group at the Grand Slam behind Michael van Gerwen. He was 5–1 down to Gerwyn Price but pulled back to 5–5 and in the latter half of the contest took out finishes of 160 and 157 and squeezed through to his only quarter-final of 2016 10–9. There, he was thrashed 16–3 by Van Gerwen. Two deciding leg successes saw Dolan get to the third round of the Players Championship Finals and he lost 10–4 to Kim Huybrechts.