[spireitematt]

E. Timmeus (1891–1895)
Gilbert Gillies (1895–1901)
E. Hind (1901–1902)
Jack Hoskins (1902–1906)
W. Furness(1906–1907)
George Swift (1907–1910)
G. Jones (1911–1913)
R. Weston(1913–1917)
T. Callaghan (1919)
J. Caffrey (1920–1922)
Harry Hadley (1922)
Harry Parkes (1922–1927)
Alec Campbell (1927)
Teddy Davison (1927–1932)
Bill Harvey (1932–1938)
Norman Bullock (1938–1945)
Bob Brocklebank (1945–1948)
Bobby Marshall (1948–1952)
Ted Davison (1952–1958)
Duggie Livingstone (1958–1962)
Tony McShane (1962–1967)
Jimmy McGuigan (1967–1973)
Joe Shaw (1973–1976)
Arthur Cox (1976–1980)
Frank Barlow (1980–1983)
John Duncan (1983–1987)
Kevin Randall (1987–1988)
Paul Hart (1988–1991)
Chris McMenemy (1991–1993)
John Duncan (1993–2000)
Nicky Law (2000–2001)
Dave Rushbury (2002–2003)
Roy McFarland (2003–2007)
Lee Richardson (2007–2009)
John Sheridan (2009–2012)
Paul Cook (2012–2015)
Dean Saunders (2015)
Danny Wilson (2015–2017)
Gary Caldwell (2017)
Jack Lester (2017–)

Norman Bullock and John Duncan 1993-2000 are the longest serving managers with 7 years each unless you add both John Duncan's spells which mean he is the longest serving manager with 11 years.

The average manager lasts about 3.2 years at Chesterfield.