The medal is voted on by players of the AFL Masters Pastimes FC and presented to the person that they feel has contributed most to the team during the season. It is named after Charlie Halkyard, who was a true pioneer for the Pastimes/Carey Park Football Club. As a player, he was a member of the Pastimes FC three peat of Premierships from 1946-48. He was awarded the Hayward’s Medal in 1948 as the best player in the competition, which was presented retrospectively in 1998. When moving into administration he was President of the Club for eight years from 1951 to 1959 and oversaw the transition from the name Pastimes after the Club decided to center its activities on the growing suburb of Carey Park in 1956. Awarded life membership in 1957 he continued to volunteer his time in many roles.
| Year | Winner |
| 2017 | Shane Jones |
| 2018 | Sean Widdeson |
| 2019 | Matthew Turpin |
| 2020 | Sean Widdeson |
| 2021 | Darren Olsen |
| 2022 | Simon Orsi |