His school Matthew Flinders Anglican College had a team which he played with, then joined the local Maroochydore Football Club.

After missing the early part of 2007 through injury, he became one of the Lions' most important players in 2007, with an impressive ability to hit targets from the kick out.

He also missed a significant amount of football after rupturing his anterior cruciate ligament during the 2010 season necessitating LARS surgery.

[5] Upon retirement from his playing career, Drummond accepted a role as a development coach with North Melbourne in late 2012.

[6] He remained at North for six seasons and transitioned into assistant coaching roles with the defensive and midfield groups before accepting returning to his home state of Queensland and accepting an assistant coaching role with the Gold Coast Suns in 2018.