Montgomery reached the semi-finals of the 2011 Winmau World Masters where he was beaten in a deciding leg by Dean Winstanley. Following his victory at 2010 edition, Montgomery had another decent run reaching the semi-finals of the Zuiderduin Masters in 2011. At the 2012 BDO World Darts Championship, Montgomery reached the second round for only the second time courtesy of a 3–1 win over Fabian Roosenbrand in the first round, but was subsequently defeated 4–1 by eventual runner-up Tony O'Shea.