 Dobbie played in Queens 2008–09 UEFA Cup campaign in August 2008, when they lost 4–2 over two legs to Danish Superliga club FC Nordsjælland in the second qualifying round.Despite being the most prolific goalscorer for the Dumfries club since Andy Thomson in the early 1990s, Chisholm elected to leave Dobbie out of the starting line-up for both matches, preferring Stewart Kean.During the 2008–09 season, Dobbie scored 23 goals in 40 matches, including four in one match in a 7–1 home league win over Clyde on 25 April 2009, with all four goals arriving during a 13-minute spell during the second half, for his second Queens hat-trick.