Painter entered the 2009 PDC World Championship as the number 17 seed. He defeated Matt Clark in the first round, winning in a sudden-death leg to become the first seeded player to progress to the second round, where he beat Carlos Rodríguez. However, in the third round he lost 4–1 to eventual champion Taylor. In the inaugural Players Championship Finals at the end of January, Painter looked to be heading for another first round exit as he went 5–2 down to Alex Roy, but he won four consecutive legs to progress to the second round, where he met second seed James Wade. This match also went to a deciding leg; Painter missed one dart at the bullseye and Wade took his chance to go through at Painter's expense. However, this performance saw Painter re-establish his place in the top 16 of the rankings, and his good form in floor events from 2008 continued – he reached two semi-finals on the PDC Pro Tour, notably in Gladbeck, Germany, where on 1 March he led Taylor 5–4 before losing 6–5.