The Phelan Medal was first awarded in 1926 for the player voted the best and fairest in the Sydney First Grade Competition. It was initially called the Ellis Medal, after the person who donated the award, E J Ellis, and at the time, the medal was forged in pure gold.
By 1932 the name had changed to the Provan Trophy after the league president of the time, A D S Provan, who also donated medallion. In 1937 the trophy was again renamed, this time to the Phelan Medal in recognition of the work, effort and commitment, Jim Phelan, acknowledged as the father of football in Sydney, had given to the code. The medal then was no longer donated but purchased by the league.
Because of WWII, the award was suspended between 1942-45 however when its presentation was resumed in 1946, the voting format had temporarily changed and as well, no actual medal was bestowed. It was not until the mid-fifties that the presentation of an actual medal was resumed and this ceremony would take place at half time of the first grade grand final. Then, the winners of the first, reserve and later Under 18/19 grades would then run a lap of honour at the grand final venue prior to the commencement of the third quarter. This arrangement changed upon the introduction of the League’s Phelan Medal Night in 1972.