Fixtures, Match Details and Final Table for Season 1999/2000:
Click here for reserve team match details
Final Table (Scottish League Division Three):
| Team | Pld | W | L | D | For | Agst | Pts |
| Queen's Park | 36 | 20 | 7 | 9 | 54 | 37 | 69 |
| Berwick Rangers | 36 | 19 | 8 | 9 | 53 | 30 | 66 |
| Forfar Athletic | 36 | 17 | 9 | 10 | 64 | 40 | 61 |
| East Fife | 36 | 17 | 11 | 8 | 44 | 39 | 59 |
| Cowdenbeath | 36 | 15 | 12 | 9 | 59 | 43 | 54 |
| Dumbarton | 36 | 15 | 13 | 8 | 53 | 51 | 53 |
| East Stirlingshire | 36 | 11 | 18 | 7 | 28 | 50 | 40 |
| Brechin City | 36 | 10 | 18 | 8 | 42 | 51 | 38 |
| Montrose | 36 | 10 | 19 | 7 | 39 | 54 | 37 |
| Albion Rovers | 36 | 5 | 24 | 7 | 33 | 75 | 22 |
Results:
10 July Squires Gate 0 East Fife 1 (Friendly)
13 July Steelend Victoria 1 East Fife 5 (Friendly)
14 July East Fife 1 Dundee United 2 (Closed Door Friendly)
18 July East Fife 0 Sheffield United 4 (Alex Doig Testimonial)
21 July East Fife 1 Kilmarnock 3 (Official Opening of New Stadium)
22 July East Fife 1 Port Vale 5 (Friendly)
24 July Kettle United 2 East Fife 3 (Friendly)
27 July East Fife 1 Falkirk 1 (Closed Door Friendly)
31 July East Fife 2 Stirling Albion 2 (8-7 Pens) (League Cup 1st Rnd)
7 August East Fife 1 Berwick Rangers 2 (League Three)
10 August Arbroath 3 East Fife 2 (Challenge Cup 1st Rnd)
14 August East Stirlingshire 0 East Fife 2 (League Three)
17 August East Fife 2 Airdrie 2 (5-4 Pens) (League Cup 2nd Rnd)
21 August East Fife 1 Dumbarton 0 (League Three)
28 August East Fife 0 Montrose 0 (League Three)
4 September Albion Rovers 1 East Fife 3 (League Three)
11 September East Fife 2 Forfar Athletic 0 (League Three)
18 September Cowdenbeath 4 East Fife 0 (League Three)
25 September East Fife 0 Queen's Park 0 (League Three)
2 October Brechin City 1 East Fife 3 (League Three)
12 October East Fife 0 Heart of Midlothian 2 (League Cup 3rd Round) (Played at Starks Park, Kirkcaldy)
16 October East Fife 1 East Stirlingshire 0 (League Three)
23 October Berwick Rangers 0 East Fife 1 (League Three)
30 October Forfar Athletic 3 East Fife 2 (League Three)
6 November East Fife 2 Cowdenbeath 3 (League Three)
14 November East Fife 1 Albion Rovers 4 (League Three)
20 November Montrose 1 East Fife 2 (League Three)
27 November East Fife 1 Brechin City 0 (League Three)
4 December Queen's Park 0 East Fife 1 (League Three)
3 January Cowdenbeath 1 East Fife 0 (League Three)
8 January - Stirling Albion 2 East Fife 1 (Scottish Cup Round Two)
15 January East Fife 1 Forfar Athletic 1 (League Three)
22 January East Fife 0 Queen's Park 0 (League Three)
5 February Brechin City 3 East Fife 1 (League Three)
12 February East Fife v Montrose (League Three) - match abandoned after 14 minutes
15 February East Fife 2 Montrose 0 (League Three)
19 February Albion Rovers 3 East Fife 1 (League Three)
26 February East Stirlingshire 1 East Fife 0 (League Three)
4 March East Fife 2 Dumbarton 1 (League Three)
11 March Forfar Athletic 0 East Fife 1 (League Three)
18 March East Fife 1 Cowdenbeath 1 (League Three)
21 March East Fife 3 Berwick Rangers 1 (League Three)
25 March Montrose 1 East Fife 1 (League Three)
28 March Dumbarton 1 East Fife 1 (League Three)
1 April East Fife 2 Albion Rovers 1 (League Three)
11 April Queen's Park 1 East Fife 0 (League Three)
15 April East Fife 1 Brechin City 1 (League Three)
22 April Berwick Rangers 0 East Fife 1 (League Three)
29 April East Fife 3 East Stirlingshire 1 (League Three)
6 May Dumbarton 2 East Fife 1 (League Three)