Phelan Medal
The Phelan Medal is an annual award given in the Sydney AFL. It is awarded to best and fairest player of the Premier Division competition each year and is named after former NSW League official James E. Phelan. It is seen to be the Sydney AFL equivalent to the Brownlow Medal.
The best and fairest player in the Sydney League was first presented an unnamed award in 1926. In 1932, Mr Aub D.S. Provan, the NSW Australian National Football League president donated a trophy titled the "Provan Trophy" to the winner. The name was changed to the Phelan Medal in 1937.
Due to the cancellation of the 2021 AFL Sydney season due to the COVID-19 outbreak across Greater Sydney, the medal was not awarded in 2021.
Multiple winners
The following players have won the Phelan Medal multiple times.| Medals | Player | Team | Seasons |
| 4 | Jack Williamson | Eastern Suburbs | 1933, 1935, 1937, 1938 |
| 4 | Rod Podbury | Bankstown/Campbelltown | 1983, 1986, 1987, 1990 |
| 2 | Billy McKoy | Sydney | 1928, 1929 |
| 2 | Cliff Barnsley | Sydney | 1940, 1941 |
| 2 | Ken Champion | North Shore/Western Suburbs | 1947, 1948 |
| 2 | Wally Bryce | Liverpool | 1954, 1955 |
| 2 | Ralph Turner | South Sydney/Sydney Naval | 1959, 1961 |
| 2 | Brian Tyler | Eastern Suburbs/South Sydney | 1969, 1974 |
| 2 | George Allen | Western Suburbs | 1973, 1975 |
| 2 | John Pilkington | Newtown | 1980, 1982 |
| 2 | Graham Jones | Western Suburbs/Baulkham Hills | 1984, 1995 |
| 2 | Troy Luff | Balmain /UNSW-ES | 2002, 2006 |
| 2 | Shaun Crane | North Shore | 2017, 2018 |
| 2 | Ned Campbell | North Shore | 2023, 2024 |
Phelan Medal wins by club
| Club | Total wins | Years |
| Balmain | 6 | 1956, 1970, 1976, 1985, 2000, 2002 |
| Bankstown | 2 | 1960, 1983 |
| Baulkham Hills/East Coast Eagles | 3 | 1995, 1998, 2016 |
| Campbelltown | 6 | 1986, 1987, 1990, 1992, 1999, 2003 |
| East Sydney/Eastern Suburbs/UNSW-ES | 13 | 1933, 1935, 1937, 1938, 1969, 1979, 1981, 1994, 2001, 2004, 2006, 2012, 2022 |
| Holroyd-Parramatta | 1 | 1989 |
| Illawarra | 2 | 1949, 1950 |
| Liverpool/Southern Districts | 6 | 1954, 1955, 1957, 1968, 1971, 1978 |
| Manly Warringah | 3 | 2013, 2015, 2023 |
| Newtown | 5 | 1936, 1946, 1972, 1980, 1982 |
| North Shore | 11 | 1930, 1939, 1947, 1951, 1962, 2005, 2017, 2018, 2022, 2023, 2024 |
| Pennant Hills | 9 | 1983, 1988, 2007, 2008, 2011, 2014, 2019, 2022, 2023 |
| South Sydney | 6 | 1934, 1952, 1958, 1959, 1964, 1974 |
| South West Sydney | 1 | 2025 |
| St George | 9 | 1931, 1932, 1965, 1977, 1991, 1992, 1993, 1997, 2022 |
| Sydney | 5 | 1926, 1928, 1929, 1940, 1941 |
| Sydney Naval | 3 | 1961, 1966, 1967 |
| Sydney University | 5 | 1953, 1990, 2009, 2010, 2020 |
| Western Suburbs/Inner-West | 7 | 1927, 1948, 1963, 1973, 1975, 1984, 1996 |