5 players with the most Best and Fairest awards in AFL history ft. Leigh Matthews 

2023 Brownlow Medal
Leigh Matthews at 2023 Brownlow Medal

The Best and Fairest award celebrates the players who performed the best over a season for their respective clubs. In the AFL, the awards are given by a player’s club in order to promote and reward good conduct.

Below is a list of five AFL players who have achieved the highest number of Best and Fairest awards so far:

5 players with the most Best and Fairest awards in AFL history

5. Michael Tuck (Six-time Best and Fairest)

Hawthorn Hawks Hall of Fame
Hawthorn Hawks Hall of Fame

Tuck's career at Hawthorn during the 1980s and early 1990s was a decorated one. He currently holds the club’s record for the most AFL games played with 426 games, most finals participated in at 39, most grand finals at 11, and the highest number of premierships at seven.

In 1986, the midfielder became the club’s coach, leading the team to four premierships. Retiring in 1992, after which his remarkable contribution to the game was honored with the Best Player in Preseason Cup Competition medal being named after him.

Michael Tuck won six Best and Fairest awards from 1976 to 1988.


4. Gary Dempsey (Six-time Best and Fairest)

AFL Rd 9 - Richmond v Western Bulldogs
AFL Rd 9 - Richmond v Western Bulldogs

Dempsey has always been recognized as one of the Western Bulldogs' all-time greats, with the honor of being one of the induction into the inaugural Bulldogs’ Hall of Fame in 2010. The former captain and six-time Best and Fairest winner (1970, 1973, 1974, 1975, 1976, and 1977) now holds club Legend status.

Dempsey’s career spanned from 1967 to 1978, in which he played 207 games and scored 105 goals. He was inducted into the Australian Hall of Fame in 1996.


3. Bill Hutchison (Seven-time Best and Fairest)

AFL Rd 9 - Essendon v GWS
AFL Rd 9 - Essendon v GWS

Hutchison made his AFL debut with Essendon on May 16, 1942, against Footscray, in Round 2 of the season.

Active from 1942 to 1957, one of the finest Rovers in the game, Hutchison amassed 496 goals in 290 games. He is a two-time All-Australian (1953 and 1956) with seven club’s Best and Fairest Awards to his name (1946, 1948, 1950, 1952, 1953, 1955, and 1956). He was selected eight times in the Sporting Life Team of the Year (1947, 1948, and 1950 to 1955).


2. Dick Reynolds (Seven-time Best and Fairest)

AFL Rd 9 - Essendon v GWS
AFL Rd 9 - Essendon v GWS

Dick Reynolds joined the Essendon Bombers at the age of 16 in 1933 from the Essendon District League, Woodlands. In his debut game, he played exceptionally well and won the club’s Best First-year Player Award. He would go on to play 320 games in the AFL.

As the VFL/AFL player with the most number of Brownlow Medals (three: in 1934, 1937, and 1938), Reynolds currently holds second place as the Essendon Bomber with the highest number of Best and Fairest winnings, seven (1934, 1936, 1937, 1938, 1939, 1942, and 1943), nearing an eighth as a runner-up in 1935. His number of Best and Fairest Awards is equal to Bill Hutchison’s.


1. Leigh Matthews (Eight-time Best and Fairest)

AFL Grand Final Premiership Cup Presenters Media Opportunity
AFL Grand Final Premiership Cup Presenters Media Opportunity

From the time of his senior debut at Hawthorn in 1969, Matthews’ story has been one to inspire. Originally recruited from Chelsea in the Bayside suburbs of Melbourne, Matthews played a total of 332 AFL matches with the Hawthorn Football Club from 1969 to 1985.

He kicked 915 goals and was the VFL’s leading goalkicker (1975) and Hawthorn’s leading goalkicker seven times (1973, 1974, 1975, 1981, 1982, 1983, and 1984). He was indeed a remarkable rover and forward.

He became captain of the Hawks in 1981, leading the team to premiership victory in 1983 after playing on the winning side in 1971, 1976, and 1978. Matthews was named Best and Fairest eight times (1971, 1972, 1974, 1976-1978, 1980 and 1982).

In addition to his achievements, he polled a cumulative 202 votes as a Brownlow Medal nominee over the course of his career, coming in third place in 1973 and 1982.

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