Dunfermline 1 Falkirk 1
Sat, 28th Aug 1999

SFL First Division:
David Moss (30) 0-1:
David Graham (73) 1-1

Dunfermline 2 Morton 1
Sat, 21st Aug 1999

SFL First Division:
Andy Smith (63) 1-0:
Andy Smith (68) 2-0:
Keith Wright (83) 2-1:

Dunfermline 4 Queens Park 0
Wed, 18th Aug 1999

CIS Insurance Cup:
Owen Coyle (20) 1-0:
Owen Coyle (39) 2-0:
Stewart Petrie (43) 3-0:
Andy Smith (81) 4-0:

Airdrie 2 Dunfermline 2
Sun, 15th Aug 1999

SFL First Division: Dunfermline travelled to North Lanarkshire for their first fixture at the Shyberry Excelsior, home of their old adversities Airdrie. An unchanged side despite the midweek set back against Morton.

Dunfermline 2 Morton 2
Tue, 10th Aug 1999

Bells Challenge Cup:
In what was one of the latest finishes to any match at East End Park (10.32pm) Morton defeated Dunfermline 5-4 on penalties after extra time.

Dunfermline 4 Inverness CT 0
Sat, 7th Aug 1999

SFL First Division:
Andy Smith (20 pen.) 1-0:
Brian Reid (62) 2-0:
Scott Thomson (81) 3-0:
Stewart Petrie (90) 4-0:

Forfar Athletic 1 Dunfermline 6
Tue, 3rd Aug 1999

Pre Season Friendly
Dunfermline: Smith (45, 62, 71), May (51), Coyle (70, 79)
Forfar Athletic: Grant (81)