Season by Season - 1960s

1969-70 Season
First Division: Winners - Colts, Runners-up - Lincluden Swifts
Second Division: Winners - Nithsdale Amateurs, Runners-up - Parkhead
League Cup: Winners  - Lincluden Swifts, Runners-up - Colts
QOS Cup: Winners - Lincluden Swifts, Runners-up - Royal Infirmary
Presidents Cup:  Winners - Nithsdale Amateurs, Runners-up - R&D
Tayleurian Cup: Winners - Lincluden Swifts, Runners-up - Lochar Thistle
Bill Brown Cup: Winners - Lincluden Swifts, Runners-up - Upper Annandale
British Legion Cup: Winners - Morton Thistle, Runners-up - Royal Infirmary
Skol Cup: Winners - Lincluden Swifts, Runners-up - Colts
Tony Pierog Shield:  Ashfield
1st Division Top Goal Scorers: Lincluden Swifts
Jack Martin, Team Losing Fewest Goals: Lincluden Swifts
2nd Division Top Goal Scorers: Nithsdale Amateurs 

1968-69 Season
First Division: Winners - Lincluden Swifts, Runners-up – Green Colts
Second Division: Winners - Morton Thistle, Runners-up – Dumfries High School FPs
League Cup: Winners - Lincluden Swifts, Runners-up – Greystone Rovers
QOS Cup: Winners - Morton Thistle, Runners-up - Lincluden Swifts 
Tayleurian Cup: Winners - Lincluden Swifts, Runners-up - Dumfries High School FPs
British Legion Cup: Winners - Lincluden Swifts, Runners-up – Green Colts
Bill Brown Cup: Winners - Dumfries High School FPs, Runners-up - Upper Annandale
Tony Pierog Shield:  Royal Infirmary

1967-68 Season
First Division: Winners – Lincluden Swifts, Runners-up – Troqueer Amateurs
QOS Cup: Winners - Mid-Annandale, Runners-up – Troqueer Amateurs 
Tayleurian Cup: Winners - Green Colts, Runners-up – Lincluden Swifts
British Legion Cup: Winners - Green Colts, Runners-up – Lincluden Swifts
Bill Brown Cup: Winners – Green Colts, Runners-up - Lincluden Swifts
Tony Pierog Shield:  Greystone Rovers 

1966-67 Season
First Division: Winners - Green Colts, Runners-up - Lincluden Swifts
Perpetual Challenge Bowl: Winners - Green Colts, Runners-up – Royal Infirmary
QOS Cup: Winners - Crichton Royal, Runners-up - Royal Infirmary
Tayleurian Cup: Winners - Kirkconnel Amateurs, Runners-up – Terregles Athletic
British Legion Cup: Winners – Green Colts, Runners-up – Troqueer Amateurs
Bill Brown Cup: Winners – Lincluden Swifts , Runners-up – Kirkconnel Amateurs

1965-66 Season
First Division: Winners - Lincluden Swifts, Runners-up – Crichton Royal
Perpetual Challenge Bowl: Winners - Lincluden Swifts, Runners-up – Green Colts
QOS Cup: Winners - Lincluden Swifts, Runners-up – Royal Infirmary 
Tayleurian Cup: Winners - Lincluden Swifts, Runners-up – Crichton Royal
British Legion Cup: Winners - Drungans Swifts, Runners-up – Crichton Royal
Bill Brown Cup: Winners – Lincluden Swifts , Runners-up – Crichton Royal

1964-65 Season
First Division: Winners - Lincluden Swifts, Runners-up – St. Andrews
Perpetual Challenge Bowl: Winners – Unknown (Final known to be between St Andrews and Lincluden Swifts or Green Colts or Crichton Royal)
QOS Cup: Winners - St Andrews, Runners-up – Noblehill  
Tayleurian Cup: Winners - Lincluden Swifts, Runners-up – Loreburn Star or St Andrews
Bill Brown Cup: Winners – Lincluden Swifts, Runners-up – Crichton Royal
British Legion Cup: Winners - Lincluden Swifts, Runners-up – Noblehill
West of Scotland Cup: Winners – Lincluden Swifts , Runners-up – Mossblown

1963-64 Season
First Division: Winners - Lincluden Swifts, Runners-up – Crichton Royal
Perpetual Challenge Bowl: Winners - Lincluden Swifts, Runners-up – Noblehill
QOS Cup: Winners - Lincluden Swifts, Runners-up – Noblehill 
Tayleurian Cup: Winners - Lincluden Swifts, Runners-up – Haley’s
British Legion Cup: Winners – Lincluden Swifts, Runners-up – Royal Infirmary
Supplementary League: Winners - Lincluden Swifts, Runners-up – St. Andrews  

1962-63 Season
First Division: Winners - Lincluden Swifts, Runners-up – Crichton Royal 
Perpetual Challenge Bowl: Winners - Lincluden Swifts, Runners-up – Loreburn Star
QOS Cup: Winners - Lincluden Swifts, Runners-up – NALGO  
Tayleurian Cup: Winners - Lincluden Swifts, Runners-up – Loreburn Star
British Legion Cup: Winners – Lincluden Swifts, Runners-up – Loreburn Star
Supplementary League: Winners - Lincluden Swifts, Runners-up – Crichton Royal
West of Scotland Cup: Winners – Lincluden Swifts,  Runners-up – Crosshill Thistle

1961-62 Season
First Division: Winners - Troqueer Amateurs, Runners-up – Loreburn Star
Perpetual Challenge Bowl: Winners - Troqueer Amateurs, Runners-up – Parkhead
QOS Cup: Winners - Troqueer Amateurs, Runners-up – Crichton Royal 
Tayleurian Cup: Winners - Troqueer Amateurs, Runners-up – Penmans United
British Legion Cup: Winners - Lincluden Swifts,  Runners-up – Crichton Royal

1960-61 Season
First Division: Winners - Penmans United, Runners-up – Troqueer Amateurs 
Perpetual Challenge Bowl: Winners - Penmans United, Runners-up – Loreburn Star
QOS Cup: Winners - Penmans United, Runners-up – Drungans Swifts  
Tayleurian Cup: Winners - Troqueer Amateurs, Runners-up – Penmans United
British Legion Cup: Winners – Troqueer Amatuers, Runners-up – Penmans United