| Top Winning Pitcher for each Season | |||
| YEAR | PITCHER | TEAM | WINS |
| 1902 | ED "DAVEY" DUNKLE | LOUISVILLE COLONELS | 30 |
| 1903 | TOM WALKER | LOUISVILLE COLONELS | 26 |
| 1904 | CHARLIE CHECH | ST. PAUL SAINTS/APOSTLES | 27 |
| 1905 | AUGUSTUS "GUS" DORNER | COLUMBUS SENATORS | 29 |
| 1906 | CHARLES "HEINIE" BERGER | COLUMBUS SENATORS | 28 |
| 1907 | GEORGE "JERRY" UPP | COLUMBUS SENATORS | 27 |
| 1908 | RICHARD "RUBE" MARQUARD | INDIANAPOLIS INDIANS | 28 |
| 1909 | GRANT "STONEY" McGLYNN | MILWAUKEE BREWERS | 27 |
| 1910 | TOM "LONG TOM" HUGHES | MINNEAPOLIS MILLERS | 31 |
| 1911 | ROY PATTERSON | MINNEAPOLIS MILLERS | 24 |
| 1912 | FRED OLMSTEAD | MINNEAPOLIS MILLERS | 28 |
| 1913 | CYRIL "CY" SLAPNICKA | MILWAUKEE BREWERS | 25 |
| 1914 | MELVIN "BERT" GALLIA | KANSAS CITY BLUES | 26 |
| 1914 | JAKE NORTHROP | LOUISVILLE COLONELS | 26 |
| 1915 | DAVID "MUTT" (D.C.) WILLIAMS | MINNEAPOLIS MILLERS | 29 |
| 1916 | EARL "CHINK" YINGLING | MINNEAPOLIS MILLERS | 24 |
| 1917 | FRANK "DIXIE" DAVIS | LOUISVILLE COLONELS | 25 |
| 1917 | GROVER "SLIM" LOWDERMILK | COLUMBUS SENATORS | 25 |
| 1918* | DICKIE KERR | MILWAUKEE BREWERS | 17 |
| 1919 | TILLER "PUG" CAVET | INDIANAPOLIS INDIANS | 28 |
| 1920 | CHARLIE "SEA LION" HALL | ST. PAUL SAINTS | 27 |
| 1921 | ADLAI "GUS" BONO | KANSAS CITY BLUES | 25 |
| 1921 | DAVE DANFORTH | COLUMBUS SENATORS | 25 |
| 1922 | TOM SHEEHAN | ST. PAUL SAINTS | 26 |
| 1923 | TOM SHEEHAN | ST. PAUL SAINTS | 31 |
| 1924 | JESS "THE SILVER FOX" PETTY | INDIANAPOLIS INDIANS | 29 |
| 1925 | BILL BURWELL | INDIANAPOLIS INDIANS | 24 |
| 1926 | GEORGE PIPGRAS | ST. PAUL SAINTS | 22 |
| 1927 | TOM SHEEHAN | KANSAS CITY BLUES | 26 |
| 1928 | ERNIE "JIM" WINGARD | MILWAUKEE BREWERS | 24 |
| 1929 | LOU "CRIP" POLLI | ST. PAUL SAINTS | 22 |
| 1930 | WILCY "CY" MOORE | ST. PAUL SAINTS | 22 |
| 1931 | FRANK "DUTCH" HENRY | MINNEAPOLIS MILLERS | 23 |
| 1932 | RUSS "SHERIFF" VAN ATTA | ST. PAUL SAINTS | 22 |
| 1932 | WILFRED "ROSY" RYAN | MINNEAPOLIS MILLERS | 22 |
| 1933 | PAUL "DAFFY" DEAN | COLUMBUS RED BIRDS | 22 |
| 1934 | WALTER TAUSCHER | MINNEAPOLIS MILLERS | 21 |
| 1935 | DOMINIC "MIKE" RYBA | COLUMBUS RED BIRDS | 20 |
| 1936 | LOU FETTE | ST. PAUL SAINTS | 25 |
| 1937 | MAX MACON | COLUMBUS RED BIRDS | 21 |
| 1938 | WHITLOW "WHIT" WYATT | MILWAUKEE BREWERS | 23 |
| 1939 | HERB "HERBIE" HASH | MINNEAPOLIS MILLERS | 22 |
| 1940 | BOB LOGAN | INDIANAPOLIS INDIANS | 18 |
| 1940 | JOHNNY LINDELL | KANSAS CITY BLUES | 18 |
| 1941 | MURRY DICKSON | COLUMBUS RED BIRDS | 21 |
| 1942 | CHARLES "BUTCH" WENSLOFF | KANSAS CITY BLUES | 21 |
| 1943 | JIM TREXLER | INDIANAPOLIS INDIANS | 19 |
| 1944 | JIM WILSON | LOUISVILLE COLONELS | 19 |
| 1944 | EARL "TEACH" CALDWELL | MILWAUKEE BREWERS | 19 |
| 1945 | OWEN SCHEETZ | MILWAUKEE BREWERS | 19 |
| 1946 | FRED SANFORD | TOLEDO MUD HENS | 15 |
| 1946 | HARRY (JAMES) TAYLOR | ST. PAUL SAINTS | 15 |
| 1946 | EWALD "LEFTY" PYLE | MILWAUKEE BREWERS | 15 |
| 1947 | CLEM "STEAMBOAT" DREISEWERD | LOUISVILLE COLONELS | 18 |
| 1948 | BOB MALLOY | INDIANAPOLIS INDIANS | 21 |
| 1949 | MEL QUEEN | INDIANAPOLIS INDIANS | 22 |
| 1949 | PHIL HAUGSTAD | ST. PAUL SAINTS | 22 |
| 1950 | HARVEY "THE KITTEN" HADDIX | COLUMBUS RED BIRDS | 18 |
| 1951 | JIM ATKINS | LOUISVILLE COLONELS | 18 |
| 1952 | EDDIE ERAUTT | KANSAS CITY BLUES | 21 |
| 1953 | GENE CONLEY | TOLEDO MUD HENS | 23 |
| * short season due to World War One | |||
