In June 2009, Painter reached the semi-finals of the UK Open, his best ever performance in the tournament. After dispatching Dennis Priestley 9–3 and Alan Tabern 10–8, Painter eventually lost 10–7 to Colin Osborne. His World Matchplay woes continued with a 13–3 defeat to Taylor in the second round of the 2009 event, though he reached the quarter-finals of the World Grand Prix and the Grand Slam of Darts, in the latter topping the 'group of death' that included Raymond van Barneveld and John Part. Another third round exit followed in the 2010 World Championship, 4–1 to van Barneveld this time.