John Thorn and John Holway selected annual winners of the "Creighton Award" from 1876, for The Pitcher (NY: Simon & Schuster, 1987). Their retroactive award is named for baseball's first superstar and first fast pitcher, Jim Creighton. Thorn and Holway referred to several new performance measures, especially "Wins Above League". Here are their selections for the 19th century, with some other "Cys" for 1900 only.
STATS, Inc., selected "retroactive" annual award winners from 1876, for The All-Time Baseball Sourcebook (1998) . I will be happy to include their 19th century Cy Young selections if someone provides them.
-pitched for first-place team
National League
1876 George Washington Bradley, SL
1877 -Tommy Bond, BOS
1878 -Tommy Bond, BOS
1879 Tommy Bond, BOS (3)
1880 John Ward, PRO
1881 George Derby, DET American Association
1882 Charles Radbourn, PRO -Will White, CIN
1883 Charles Radbourn, PRO Will White, CIN (2) Union Association
1884 -Charles Radbourn, PRO (3) Guy Hecker, LOU Hugh Daily, CHI
1885 -John Clarkson, CHI -Bob Caruthers, SL
1886 Charlie Ferguson, PHI -Dave Foutz, SL
1887 John Clarkson, CHI Matt Kilroy, BAL
1888 -Tim Keefe, NY -Silver King, SL
1889 John Clarkson, BOS (3) -Bob Caruthers, BRO (2) Players' League
1890 Bill Hutchison, CHI -Scott Stratton, LOU Silver King, CHI
1891 Bill Hutchison, CHI (2) -George Haddock, BOS
1892 Cy Young, CLE (career total, 4, inclg 1901-1903)
1893 Amos Rusie, NY
1894 Amos Rusie, NY (2)
1895 Pink Hawley, PIT
1896 Kid Nichols, BOS
1897 -Kid Nichols, BOS
1898 -Kid Nichols, BOS (3)
1899 Vic Willis, BOS (career total, 2, inclg 1901)
1900 -Joe McGinnity, BRO (career total, 2, inclg 1904)
Other selections for NL1900:
-Joe McGinnity, BRO [SABR members, BRJ 1988]
-Joe McGinnity, BRO [Bill Deane, TB 1989-]
See 1900-1919 selections from four sources.
Scope. Thorn & Holway named Creighton Award winners for each major
league season 1876-1987. Because better records are available today, I am
sure they would name 1871-1875 winners, although MLB does not recognize the
National Association as "major". Selections by SABR poll and by Bill Deane
for Total Baseball begin in 1900. Selections by STATS, Inc. (1998) begin in
1876, but I do not know them. For more information on SABR, Deane/TB, and
STATS selections, see Cy Young Award,
Hypothetical Winners 1900-1919.
First-Place winners. 15 of 37 Creighton winners pitched for teams that won league pennants, including 8 of 25 in the NL and 7 of 10 in the AA.
Last-Place winners. None of the Creighton winners pitched for a team that finished last in the league. For most of the 19th century, pitcher workloads were great enough that a plausible candidate for the season's best pitcher could carry a team at least to mediocrity. (In 1972, the baseball writers honored Steve Carlton from the last-place Philadelphia Phillies. He also won the 1972 Creighton Award.)
Repeat winners. Bond, Radbourn, Clarkson, and Nichols each won three Creighton Awards for 19th century work. Young won one in the 19th century and three more in the 20th.