Season by Season - 1950s

1959-60 Season
First Division: Winners - Western Thistle, Runners-up – Troqueer Amateurs
Perpetual Challenge Bowl: Winners - Troqueer Amateurs, Runners-up – Unknown
QOS Cup: Winners - Hearts of Heath, Runners-up – Drungans Swifts 
Tayleurian Cup: Winners - Hearts of Heath, Runners-up – Penmans United
British Legion Cup: Winners – Western Thistle, Runners-up – Hearts of  Heath

1958-59 Season
First Division: Winners - Troqueer Amateurs, Runners-up – Hearts of Heath
Perpetual Challenge Bowl: Winners - Troqueer Amateurs, Runners-up – Drungans Swifts
QOS Cup: Winners - Troqueer Amateurs, Runners-up – Hearts of Heath 
Tayleurian Cup: Winners - Troqueer Amateurs, Runners-up – Hearts of Heath

1957-58 Season
First Division: Winners - Not awarded
Perpetual Challenge Bowl: Winners - Troqueer Amateurs, Runners-up – Unknown
QOS Cup: Winners - Drungans Swifts, Runners-up – Hearts of Heath   
Tayleurian Cup: Winners - Unknown (Final known to be between Lincluden and Hearts of Heath or Troqueer Amateurs)

1956-57 Season
First Division: Winners - Hearts of Heath, Runners-up – Millbrae   
Perpetual Challenge Bowl: Winners – Maxwelltown Thistle, Runners-up – Unknown
Tayleurian Cup: Winners - Hearts of Heath , Runners-up – Millbrae

1955-56 Season
First Division: Winners - Lincluden, Runners-up – Maxwelltown Thistle
Perpetual Challenge Bowl: Winners - Maxwelltown Thistle, Runners-up – Lincluden
Tayleurian Cup: Winners - Millbrae , Runners-up – Hearts of Heath 

1954-55 Season
First Division: Winners - Dumfries Amateurs, Runners-up – Hearts of Heath 
Perpetual Challenge Bowl: Winners - RAF, Runners-up – Maxwelltown Thistle
Tayleurian Cup: Winners - Lincluden, Runners-up – Maxwelltown Thistle