Montgomery won the 2010 British Classic as well as the 2010 Zuiderduin Masters, his inaugural major title, where he came from 4–0 down in sets to win 5–4 against Robbie Green, also surviving three match darts. Montgomery finished as the year end number one in WDF Working Rankings Europe for 2010. At the 2011 BDO World Darts Championship, Montgomery was beaten 3–1 in sets by Alan Norris.