The 6'5", 205 lbs. rearguard joined the OJHL as a 17-year old rookie in 2008-09, recording a respectible 11 points in 41 regular season games and would follow that up with 20 points to lead all Caps defencemen in scoring. A trade during the summer of 2010 would see Cummings join the Villanova Knights, and although his offensive totals dropped, he was a rock on the blueline for one of the year's suprising clubs, ultimately falling in the quarter-final to the eventual league champion Wellington Dukes.
This season saw Cummings begin as the Flyers captain, notching 11 points before the trade to Wellington. While with the Dukes, Cummings would record just a single assist, but was one of the club's key shutdown guys as they entered the playoffs.