1939-40
Pittsfield Regional Champs Coach's name & record needed
Milton District Tournament
Title Game lost to Pearl 36-32
Top 2 Teams From District Advanced to Regional
Pittsfield
Regional Champions
1st Rd Beat Perry 54-28
Semi-final Beat Winchester 45-25
Title Game Beat Pittsfield 30-29
Quincy
Sectional Tournament
1st Rd Beat Jacksonville I.S.D.
Semi-final lost to Beardstown 37-29
Beardstown Beat Camp Point in title game
Beardstown lost to Salem in Sweet 16
1940-41 Nebo
District Champions Coach's name & record needed
1st Rd Beat Nebo 31-17
Semi-final Beat New Canton 51-19
Title Game Beat Hull 38-19
Pittsfield Regional Tournament
1st Rd lost to Griggsville 29-28
Pittsfield beat Winchester in title game
1941-42
Nebo District Champions Coach's name &
record needed
Early Rd Scores Needed
Title
Game Beat Nebo 49-23
Pittsfield Regional Tournament
1st Rd lost to Perry 36-34
Winchester beat Pittsfield in title game
1942-43 Milton
District Runner-Up Coach's name & record needed
1st Rd Beat Kinderhook 60-23
Semi-final
Beat Pearl 44-22
Title Game lost to Nebo 31-27
1943-44 Milton
District Runner-Up Coach's name & record needed
Early Rd Scores Needed
Title Game lost to Nebo 31-27
1944-45
Milton District Champions Coach's name & record needed
Semi-final
Beat New Canton 32-28
Title
Game Beat Nebo 21-20 (O/T)
Pittsfield Regional Tournament
Regional Scores Needed
1945-46 Milton
District Runner-Up Coach's name & record needed
Early Rd Scores Needed
Title Game lost to Kinderhook 30-27
1946-47
Milton District Champions Coach's name & record needed
Semi-final
Beat Perry 42-27
Title Game Beat Pearl 45-34
Pittsfield Regional Tournament
1st Rd lost to Winchester 47-31
Pittsfield beat Winchester in title game
1947-48
Pittsfield Regional Tourney Coach's name & record needed
1st Rd lost to Alsey 44-42
Pittsfield beat Winchester in title game
1948-49
Pittsfield Regional Tourney Coach's name & record needed
1st Rd lost to Pittsfield 40-24
Pittsfield beat Winchester in title game
1949-50
Pittsfield Regional Tournament Coach's name & record needed
1st Rd Beat Pearl 48-34
Semi-final lost to Winchester 42-41
Winchester beat Pittsfield in title game
1950-51
Barry Regional Tournament Coach's name & record needed
Milton Scores Needed
Griggsville
beat Pittsfield in title game
1951-52
Pittsfield Regional Tourney Coach's name & record needed
1st Rd lost to Pittsfield 60-50
Perry beat Pleasant Hill in title game
1952-53
Pittsfield Regional Tourney Coach's name & record needed
1st Rd lost to Winchester 66-46
Pittsfield beat Perry in title game
1953-54
Pittsfield Regional Tourney Coach's name & record needed
1st Rd lost to Perry 69-33
Griggsville beat Pittsfield in title game
1954-55 Pleasant
Hill Regional Tourney Coach's name & record needed
**1st Rd lost to Pittsfield 73-39
PITTSFIELD (73): Fox 25, Dunham 23, Sanderson 12, Fraizer 8, Ferguson 5, Bagent 3.
MILTON (39): Kern 17, Hoover 11, Smart 4, Bissell 3, Ranfo 3, McEuen 1.
Winchester beat Pittsfield in title game
**Final boys basketball game for Milton High School. Consolidated with Pearl in the summer of 1955 to form Milton East
Pike High School.