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