Following his efforts at the National Championships, the newly formed Gold Coast Football Club signed him as one of their two priority zone selections from the Northern Territory.

May would finish the 2010 season for Melbourne Grammar in the Associated Public Schools of Victoria competition with 40 goals from eight games, as well as the best and fairest award.

[4] On 16 April 2016, May knocked out Stefan Martin after leaving his feet to deliver a full-body hit after the ball had gone by.

[6] May was named co-captain of the Gold Coast Football Club in December 2016, making him just the sixth indigenous captain in VFL/AFL history.

However, since the initial year, his impact and contribution to the Melbourne backline has been outstanding alongside Jake Lever and Adam Tomlinson .

[9][10] In June 2022, May was suspended for one match following a public altercation with teammate Jake Melksham and also drinking alcohol while under the concussion protocols.