Season by Season 1990s

1999-2000 Season
First Division: Winners - Dumfries Amateurs, Runners-up - YMCA
Second Division: Winners - Abbey Vale, Runners-up - Lochar Thistle
League Cup:  Winners - Kirkconnel Amateurs, Runners-up - Dumfries Amateurs
QOS Cup: Winners - Mid-Annandale, Runners-up - Abbey Vale
Presidents Cup: Winners - Abbey Vale, Runners-up - Kirkton AFC
Tayleurian Cup: Winners - Kirkconnel Amateurs, Runners-up - Abbey Vale
Nivision Cup: Winners - Nithsdale Amateurs, Runners-up - Abbey Vale
British Legion Cup: Winners - Mid-Annandale, Runners-up - Kirkconnel Amateurs
McCall Cup: Winners - Abbey Vale, Runners-up - Lochar Thistle
Burns Cup: Winners - Lochmaben, Runners-up - Dumfries Amateurs
Tony Pierog Shield: Terregles Athletic
1st Division Top Goal Scorers: Dumfries Amateurs
Jack Martin, Team Losing Fewest Goals: Abbey Vale & Kirkconnel Amateurs
2nd Division Top Goal Scorers: Lochar Thistle & Terregles Athletic
Flesher’s 5-A-Sides: YMCA 

1998-99 Season
First Division: Winners - Kirkconnel Amateurs, Runners-up - YMCA
Second Division: Winners - Dumfries Amateurs, Runners-up - Kirkpatrick Fleming
League Cup: Winners - Kirkconnel Amateurs, Runners-up - Nithsdale Amateurs
QOS Cup: Winners - Kirkconnel Amateurs, Runners-up - Upper Annandale
Presidents Cup:  Winners - Dumfries Amateurs, Runners-up - Terregles Athletic
Tayleurian Cup: Winners - YMCA, Runners-up - Mid-Annandale
Nivision Cup: Winners - Loreburn, Runners-up - Nithsdale Amateurs
British Legion Cup: Winners - Kirkconnel Amateurs, Runners-up - Kirkpatrick Fleming
McCall Cup: Winners - Noblehill, Runners-up - Dumfries Amateurs
Burns Cup: Winners - Loreburn, Runners-up - Kirkconnel Amateurs
Tony Pierog Shield: Abbey Vale
1st Division Top Goal Scorers: Loreburn & YMCA
Jack Martin, Team Losing Fewest Goals: Kirkconnel Amateurs
2nd Division Top Goal Scorers: Dumfries Amateurs
Flesher’s 5-A-Sides: Dumfries  Amateurs

1997-98 Season
First Division: Winners - Kirkconnel Amateurs, Runners-up - Nithsdale Amateurs
Second Division: Winners - Mid-Annandale, Runners-up - Loreburn AFC
League Cup: Winners - Mid-Annandale, Runners-up - YMCA
QOS Cup: Winners - Mid-Annandale, Runners-up - Kirkconnel Amateurs
Presidents Cup:  Winners - Mid-Annandale, Runners-up - Dumfries Amateurs
Tayleurian Cup: Winners - Kelloholm, Runners-up - Loreburn AFC
Nivision Cup: Winners - Upper Annandale, Runners-up - Morton Thistle
British Legion Cup: Loreburn, Runners-up - Lochar Thistle
McCall Cup: Winners - Mid-Annandale, Runners-up - Loreburn AFC
Burns Cup: Winners - YMCA, Runners-up - Abbey Vale
Tony Pierog Shield: Kirkpatrick Fleming
1st Division Top Goal Scorers: Abbey Vale
Jack Martin, Team Losing Fewest Goals: Mid-Annandale & Kirkconnel Amateurs
2nd Division Top Goal Scorers: Mid-Annandale
Flesher’s 5-A-Sides: Lochar Thistle 

1996-97 Season
First Division: Winners - Kirkconnel Amateurs, Runners-up – Nithsdale Amateurs
Second Division: Winners - Lochar Thistle, Runners-up - Morton Thistle
League Cup: Winners – Nithsdale Amateurs, Runners-up - YMCA
QOS Cup: Winners - Kirkconnel Amateurs, Runners-up - Kirkpatrick Fleming
Presidents Cup:  Winners - Lochar Thistle, Runners-up - Eastriggs
Tayleurian Cup: Winners - Lochmaben, Runners-up - YMCA
Nivision Cup: Winners - Lochmaben, Runners-up - Kirkton
British Legion Cup: Kirkconnel Amateurs, Runners-up - YMCA
McCall Cup: Winners - Eastriggs, Runners-up - Lochar Thistle
Tony Pierog Shield: Noblehill
1st Division Top Goal Scorers: Nithsdale Amateurs & Kirkconnel Amateurs
Jack Martin, Team Losing Fewest Goals: Morton Thistle
2nd Division Top Goal Scorers: Lochar Thistle
Flesher’s 5-A-Sides: Lochmaben 

1995-96 Season
First Division: Winners - Lochmaben, Runners-up - Abbey Vale
Second Division: Winners - Kirkpatrick Fleming, Runners-up - Kelloholm
League Cup: Winners - Lochmaben, Runners-up - Kelloholm
QOS Cup: Winners - YMCA, Runners-up - Nithsdale Amateurs
Presidents Cup:  Winners - Kirkton, Runners-up - Kirkpatrick Fleming
Tayleurian Cup: Winners - Nithsdale Amateurs, Runners-up - Lochmaben
Nivision Cup: Winners - Lochmaben, Runners-up - Kirkton
British Legion Cup: Nithsdale Amateurs, Runners-up - Kirkconnel Amateurs
McCall Cup: Winners - Kirkpatrick Fleming, Runners-up - Eastriggs
Supplementary Cup:  Winners - Kirkpatrick Fleming, Runners-up - Kirkton
Tony Pierog Shield: YMCA
1st Division Top Goal Scorers: Nithsdale Amateurs 
Jack Martin, Team Losing Fewest Goals: Lochmaben
2nd Division Top Goal Scorers: Kelloholm
Flesher’s 5-A-Sides: YMCA 

1994-95 Season
First Division: Winners - Lincluden Colts, Runners-up - Kirkconnel Amateurs
Second Division: Winners - Lochar Thistle, Runners-up - Mid-Annandale
League Cup: Winners - Kirkconnel Amateurs, Runners-up - Lincluden Colts
QOS Cup: Winners - Kirkconnel Amateurs, Runners-up - Lochmaben
Presidents Cup:  Winners - Mid-Annandale, Runners-up - Lochar Thistle
Tayleurian Cup: Winners - Nithsdale Amateurs, Runners-up - YMCA
Nivision Cup: Winners - YMCA, Runners-up - Lincluden Colts
British Legion Cup: Lincluden Colts, Runners-up - Mid-Annandale
McCall Cup: Winners - Mid-Annandale, Runners-up - Lochar Thistle
Tony Pierog Shield: Lochar Thistle
1st Division Top Goal Scorers: Lincluden Colts
Jack Martin, Team Losing Fewest Goals: Eastriggs
2nd Division Top Goal Scorers: Lochar Thistle
Flesher’s 5-A-Sides: YMCA 

1993-94 Season
First Division: Winners - Kirkconnel Amateurs, Runners-up - Lincluden Colts
Second Division: Winners - Morton Thistle, Runners-up - Kirkton
League Cup: Winners - Kirkconnel Amateurs, Runners-up - Dumfries HS FPs
QOS Cup: Winners - Kirkconnel Amateurs, Runners-up - Abbey Vale
Presidents Cup:  Winners - Hoddam Rangers, Runners-up - Lochar Thistle
Tayleurian Cup: Winners - Kirkconnel Amateurs, Runners-up - YMCA
Nivision Cup: Winners - Abbey Vale, Runners-up - Mid-Annandale
British Legion Cup: YMCA, Runners-up - Lochmaben
McCall Cup: Winners - Max High FPs Amateurs, Runners-up - Kirkpatrick Fleming
Tony Pierog Shield: Kirkpatrick Fleming
1st Division Top Goal Scorers: Lincluden Colts
Jack Martin, Team Losing Fewest Goals: Kirkconnel Amateurs
2nd Division Top Goal Scorers: Morton Thistle
Flesher’s 5-A-Sides: YMCA 

1992-93 Season
First Division: Winners - YMCA, Runners-up - Lincluden Colts
Second Division: Winners – Glenmarlin Thistle, Runners-up - Glaxochem
League Cup: Winners - Dumfries Academy FPs, Runners-up - Lochar Thistle
Queen of the South Cup: Winners - Lincluden Colts, Runners-up - Upper Annandale
Presidents Cup:  Winners - Kirkpatrick Fleming, Runners-up - Mid-Annandale
Tayleurian Cup: Winners - Abbey Vale, Runners-up - Upper Annandale
Nivision Cup: Winners - Dumfries Academy FPs, Runners-up - Upper Annandale
British Legion Cup: Dumfries High School FPs, Runners-up - Abbey Vale
McCall Cup: Winners – Glenmarlin Thistle, Runners-up - Kirkpatrick Fleming,
Tony Pierog Shield: Noblehill
1st Division Top Goal Scorers: Abbey Vale
Jack Martin, Team Losing Fewest Goals: Mid-Annandale
2nd Division Top Goal Scorers: Glenmarlin Thistle
Flesher’s 5-A-Sides: Galloway Rovers 

1991-92 Season
First Division: Winners - YMCA, Runners-up - Kirkconnel Amateurs
Second Division: Winners - Lochmaben, Runners-up - Hoddam Rangers
League Cup: Winners - YMCA, Runners-up - Kirkconnel Amateurs
Queen of the South Cup: Winners - Galloway Rovers, Runners-up - Glenmarlin Thistle
Presidents Cup:  Winners - Glenmarlin Thistle, Runners-up - St.Joseph’s College FPs
Tayleurian Cup: Winners - Kirkconnel Amateurs, Runners-up - Dumfries Academy FPs
Bill Nivision Memorial Cup: Winners - YMCA, Runners-up - Abbey Vale
British Legion Cup: Lincluden Colts, Runners-up - Upper Annandale
McCall Cup: Winners - Lochmaben, Runners-up - Noblehill
Tony Pierog Shield: Glaxochem
1st Division Top Goal Scorers: Kirkconnel Amateurs
Jack Martin, Team Losing Fewest Goals: Kirkconnel Amateurs
2nd Division Top Goal Scorers: Lochmaben
Flesher’s 5-A-Sides: Heathhall Hearts 

1990-91 Season
First Division: Winners - Kirkconnel Amateurs, Runners-up - YMCA
Second Division: Winners - Upper Annandale, Runners-up - Lochar Thistle
League Cup: Winners - Nithsdale Amateurs, Runners-up - Upper Annandale
QOS Cup: Winners - Kirkconnel Amateurs, Runners-up - Dumfries High School FPs
Presidents Cup:  Winners - Upper Annandale, Runners-up - Heathhall Hearts
Tayleurian Cup: Winners - Dumfries High School FPs, Runners-up - Nithsdale Amateurs
Nivision Cup: Winners - Abbey Vale, Runners-up - Mid-Annandale
British Legion Cup: YMCA, Runners-up - Lincluden Colts
McCall Cup: Winners - Upper Annandale, Runners-up - Terregles Athletic
Tony Pierog Shield: Lochar Thistle
1st Division Top Goal Scorers: Kirkconnel Amateurs
Jack Martin, Team Losing Fewest Goals: Kirkconnel Amateurs
2nd Division Top Goal Scorers: Heathhall Hearts
Flesher’s 5-A-Sides: Kirkconnel Amateurs