[1] Montgomery joined the WANFL umpiring panel in 1950 and was soon umpiring league football, making his debut in a match between East Fremantle and Swan Districts at Fremantle Oval in Round 4 of the 1952 season.
[6] During Round 1 of the 1956 season Montgomery reported Jack Sheedy for using abusive language towards him, to which Sheedy responded at the tribunal by swearing on a bible that Montgomery had reported the wrong player.
He alleged that as he was walking out of the ground, a player drove a car toward him, attempting to run him over.
[9][10] He retired in 1972 having umpired 308 WANFL league matches including five grand finals.
[4] The award for best WAFL field umpire is named the Ray Montgomery Medal in his honour.