Dunfermline 2 Ayr United 1
Sat, 25th Sep 1999

SFL First Division:
Owen Coyle (9) 1-0:
Owen Coyle (10) 2-0:
Glynn Hurst (55) 2-1:

Raith Rovers 2 Dunfermline 2
Sat, 18th Sep 1999

SFL First Division: Dunfermline welcomed the first local derby with Raith with the expectation that the four straight wins in a row two seasons ago could be converted into a famous five. Pars supporters entered Starks Park with various printed versions of the number 5 on cards tucked under their arms.

Dunfermline 1 St Mirren 1
Sat, 11th Sep 1999

SFL First Division:
Tommy Brown (33) 0-1:
Richard Huxford (45) 1-1:

Livingston 0 Dunfermline 1
Sat, 4th Sep 1999

SFL First Division: Dick Campbell brought new signing from Hibs Justin Skinner into his starting line up; Scott Thomson was out injured so Richard Huxford was the latest attempt at finding a right back and Eddie May found himself relegated to the subs bench.