Initially, the chairman/mayor was chosen by the elected councillors from among themselves.
Later, it became a separate role elected by the public.

The chairmen and mayors of the Winton Divisional Board and the Winton Shire Council include: 
1887–1889 J. B. Riley
1889–1890 Robert Christian Ramsay
1890–1891 M. F. Ramsay
1891–1898 A. G. Fraser
1898–1901 Robert Christian Ramsay (2nd term)
1901-1901 William Henry Corfield
1901–1903 Robert Logan Chirnside
1903–1907 Robert Christian Ramsay (3rd term)
1907–1910 Arthur Douglas Ramsay
1910–1912  W. H. Cameron
1913–1920 Andrew John Baxter McMaster
1920–1921 Robert Edward Jackson
1921–1924 Andrew John Baxter McMaster (2nd term)
1924–1927 Leonard Irving
1927–1930 Percy Neil Grieve
1930–1934 John Rupert Wilfred Kennedy
1934–1946 Thomas Joseph Shanahan
1946–1955 Edward Charles Pender Phillott
1955–1958 Walter de Levante Booty
1958–1964 Edward Charles Pender Phillott (2nd term)
1964–1976 Charles Kempson Maxwell
1976–1981 William Joseph Harold Holmes
1981–1987 Eric Barton Bryce
1987–1995 Erice Muir Lenton
1995–2007  S. B. (Bruce) Collins
2008–2012 Edward Lawrence (Ed) Warren
2012–2017 Graham Thomas (Butch) Lenton (died in office)
2017–present: Gavin John Baskett
In the 2008 election, the two candidates Ed Lawrence and Butch Lenton received the same number of votes.
The winner, Ed Lawrence, was decided by drawing a name from a hat.

In the 2016 election Butch Lenton was elected unopposed.
He died in office on 1 October 2017 in Winton, which resulted in a by-election.
He was posthumously named as one of the Queensland Greats by Queensland Premier Annastacia Palaszczuk in a ceremony at the Queensland Art Gallery on 8 June 2018.
Initially, the chairman/mayor was chosen by the elected councillors from among themselves. Later, it became a separate role elected by the public.
The chairmen and mayors of the Winton Divisional Board and the Winton Shire Council include: 
1887–1889 J. B. Riley
1889–1890 Robert Christian Ramsay
1890–1891 M. F. Ramsay
1891–1898 A. G. Fraser
1898–1901 Robert Christian Ramsay (2nd term)
1901-1901 William Henry Corfield
1901–1903 Robert Logan Chirnside
1903–1907 Robert Christian Ramsay (3rd term)
1907–1910 Arthur Douglas Ramsay
1910–1912  W. H. Cameron
1913–1920 Andrew John Baxter McMaster
1920–1921 Robert Edward Jackson
1921–1924 Andrew John Baxter McMaster (2nd term)
1924–1927 Leonard Irving
1927–1930 Percy Neil Grieve
1930–1934 John Rupert Wilfred Kennedy
1934–1946 Thomas Joseph Shanahan
1946–1955 Edward Charles Pender Phillott
1955–1958 Walter de Levante Booty
1958–1964 Edward Charles Pender Phillott (2nd term)
1964–1976 Charles Kempson Maxwell
1976–1981 William Joseph Harold Holmes
1981–1987 Eric Barton Bryce
1987–1995 Erice Muir Lenton
1995–2007  S. B. (Bruce) Collins
2008–2012 Edward Lawrence (Ed) Warren
2012–2017 Graham Thomas (Butch) Lenton (died in office)
2017–present: Gavin John Baskett
In the 2008 election, the two candidates Ed Lawrence and Butch Lenton received the same number of votes. The winner, Ed Lawrence, was decided by drawing a name from a hat.
In the 2016 election Butch Lenton was elected unopposed. He died in office on 1 October 2017 in Winton, which resulted in a by-election. He was posthumously named as one of the Queensland Greats by Queensland Premier Annastacia Palaszczuk in a ceremony at the Queensland Art Gallery on 8 June 2018.
Shire of Winton