Drummond grew up in Mooroopna, a Victorian country town 181 kilometers north of Melbourne. He played junior football with the local Mooroopna Football Netball Club. As a teenager, Drummond moved to Melbourne to board at Melbourne Grammar on one of the school's Indigenous scholarships. He travelled home regularly though, including to player with the Murray Bushrangers in the TAC Cup in 2013. He also played for the Victorian Country side that year, representing the team at 2013 National Championships. Despite strong form in his underage years, Drummond passed unselected through the national and rookie drafts in 2013. In 2014, he returned to the family home in country Victoria, taking up a part-time job at a sports store and playing again for the Bushrangers. Drummond ultimately won the club's best and fairest award for his performances that season. In addition, he played three matches with the Richmond Football Club's VFL side that year. Drummond impressed at the 2014 draft combine, recording top three results in the repeat sprint, beep test, standing vertical jump, goalkicking and clean hands tests.
AFL career
Drummond was drafted by Richmond with the club's third pick and 52nd selection overall in the 2014 AFL draft. He made his debut in round 4, 2015 against the Melbourne Football Club. He was stretchered from the ground during the second quarter however, after injuring his right knee in a marking contest. The subsequent diagnosis of a severe anterior cruciate ligament injury resulted in a season ending knee operation. Drummond returned to football in 2016 through the club's reserves side in the VFL. He made his return at AFL level in round 18 against at the MCG. He kicked his first career goal in the match, as well as recording 10 disposals. He was dropped from senior side following four consecutive matches however and would return to the VFL to play out his year with the reserves. Drummond finished the season with averages of 9.8 disposals and 4.5 tackles per game across his four appearances. In April 2017 Drummond suffered an injury to his knee while playing with Richmond's reserves side in the VFL. Subsequent scans revealed he had torn his anterior cruciate ligament again, though this time on his left knee. The injury would end his season prematurely for the second time in two years and kept him from playing AFL football that year. Drummond's second injury rehabilitation progressed faster than with his first knee reconstruction, having completing lengthy running drills by early December 2017. His summer also included a role change, with coaches shifting him into a hybrid forward-midfield position. Initial estimates had Drummond to return to full skills work by the first week of February with a return to full fitness and selection consideration in time for round 1 of the AFL season. He missed this deadline by one week however, making his return through a practice match in the VFL in late March. After five matches at the reserves level Drummond suffered a hamstring strain in a VFL match against. He missed three matches as a result of the injury before making his return to VFL football in early June. Later that month he suffered a re-occurrence of his earlier hamstring strain while completing a club training session. Drummond returned to training in July but suffered a third hamstring strain in the same location before he could make a return to match play. He spent the back-half of August on light training duties while club officials considered him some chance to return in time for the club's VFL finals series. Drummond's return to full fitness would come too late however, with the club's VFL season ended in the second round of the finals series following consecutive losses to and. He had managed just seven games at the reserves level and did not play an AFL match in 2018. Drummond was delisted at season's end, after a four year stint at the club that included playing in five AFL matches.
