| 20/07/1999 | Marlow | Friendly | | Away | W | 1-0 | 265 | M. Harkin 6 | |
| 21/07/1999 | Oxford City | Friendly | | Away | W | 3-0 | 393 | Own Goal 74 S. Brown 76 S. Brown 87 | |
| 27/07/1999 | Thame United | Friendly | | Away | L | 0-1 | 280 | | |
| 28/07/1999 | Nottingham Forest | Friendly | | Home | W | 2-0 | 2198 | S. Devine 37 P. Emblen 67 | |
| 30/07/1999 | Hayes | Friendly | | Away | L | 0-3 | 450 | | |
| 31/07/1999 | Peterborough United | Friendly | | Home | W | 2-0 | 979 | P. Emblen 10 J. McSporran 88 | |
| 07/08/1999 | Burnley | Nationwide League Division 2 | | Home | D | 1-1 | 6115 | J. McSporran 28 | |
| 10/08/1999 | Wolverhampton Wanderers | Worthington Cup | 1 1st Leg | Home | L | 0-1 | 4564 | | |
| 11/08/1999 | Aylesbury United | Friendly | | Away | L | 1-2 | 450 | D. Senda 38 | |
| 14/08/1999 | Scunthorpe United | Nationwide League Division 2 | | Away | W | 1-0 | 4092 | S. Devine 42 | |
| 21/08/1999 | Preston North End | Nationwide League Division 2 | | Home | D | 1-1 | 5091 | S. Devine 28 | |
| 24/08/1999 | Wolverhampton Wanderers | Worthington Cup | 1 2nd Leg | Away | W | 4-2 | 13723 | Own Goal 10 J. McSporran 25 J. McSporran 59 K. Ryan 83 | Agg 4-3 |
| 28/08/1999 | Gillingham | Nationwide League Division 2 | | Away | D | 2-2 | 6180 | S. Brown 34 (Pen) P. McCarthy 80 | |
| 31/08/1999 | Wrexham | Nationwide League Division 2 | | Home | L | 0-1 | 5393 | | |
| 01/09/1999 | Peterborough United | Avon Insurance Combination | | Home | L | 0-2 | 0 | | |
| 04/09/1999 | Oxford United | Nationwide League Division 2 | | Away | D | 0-0 | 6306 | | |
| 08/09/1999 | Cambridge United | Avon Insurance Combination | | Away | L | 0-2 | 60 | | |
| 11/09/1999 | Cardiff City | Nationwide League Division 2 | | Home | W | 3-1 | 4982 | M. Lawrence 19 J. McSporran 76 A. Baird 79 | |
| 14/09/1999 | West Bromwich Albion | Worthington Cup | 2 1st Leg | Away | D | 1-1 | 9383 | P. McCarthy 58 | |
| 15/09/1999 | Bristol Rovers | Avon Insurance League Cup | 1 | Home | D | 1-1 | 0 | R. Thompson 78 | |
| 18/09/1999 | Bury | Nationwide League Division 2 | | Away | L | 0-2 | 3293 | | |
| 21/09/1999 | West Bromwich Albion | Worthington Cup | 2 2nd Leg | Home | L | 3-4 | 5047 | S. Devine 4 D. Carroll 70 S. Brown 120 (Pen) | aet |
| 22/09/1999 | Northampton Town | Avon Insurance Combination | | Home | D | 0-0 | 0 | | |
| 25/09/1999 | Blackpool | Nationwide League Division 2 | | Away | W | 2-1 | 3452 | J. McSporran 38 S. Devine 42 | |
| 02/10/1999 | Reading | Nationwide League Division 2 | | Home | W | 5-3 | 7042 | K. Ryan 7 D. Carroll 45 S. Devine 52 S. Devine 69 S. Devine 83 | |
| 06/10/1999 | Luton Town | Avon Insurance Combination | | Away | L | 2-5 | 140 | D. Senda 8 (Pen) A. Baird 54 | |
| 09/10/1999 | Cambridge United | Nationwide League Division 2 | | Home | W | 1-0 | 5345 | S. Devine 7 | |
| 12/10/1999 | Barnet | Avon Insurance Combination | | Home | W | 2-1 | 0 | M. Harkin 30 D. Senda 85 | |
| 16/10/1999 | Notts County | Nationwide League Division 2 | | Away | L | 1-2 | 5710 | S. Devine 20 | |
| 19/10/1999 | Luton Town | Nationwide League Division 2 | | Away | D | 1-1 | 5820 | J. Cousins 24 | |
| 23/10/1999 | Blackpool | Nationwide League Division 2 | | Home | L | 0-2 | 5021 | | |
| 26/10/1999 | Leyton Orient | Avon Insurance Combination | | Home | L | 0-1 | 0 | | |
| 30/10/1999 | Oxford City | F.A. Challenge Cup | 1 | Home | D | 1-1 | 2963 | M. Simpson 67 | |
| 02/11/1999 | Oldham Athletic | Nationwide League Division 2 | | Away | D | 2-2 | 3807 | S. Devine 2 A. Baird 88 | |
| 06/11/1999 | Bristol Rovers | Nationwide League Division 2 | | Home | D | 1-1 | 5267 | S. Devine 67 | |
| 09/11/1999 | Oxford City | F.A. Challenge Cup | abandoned | Home | Abandoned | | | | |
| 12/11/1999 | Wigan Athletic | Nationwide League Division 2 | | Away | L | 1-2 | 5523 | J. McSporran 26 | |
| 16/11/1999 | Oxford City | F.A. Challenge Cup | 1 Rep | Neutral | W | 1-0 | 4004 | S. Brown 51 | At Oxford United |
| 20/11/1999 | Wigan Athletic | F.A. Challenge Cup | 2 | Home | D | 2-2 | 2992 | S. Devine 20 K. Ryan 91 | |
| 23/11/1999 | Stoke City | Nationwide League Division 2 | | Home | L | 0-4 | 4345 | | |
| 24/11/1999 | Fulham | Avon Insurance Combination | | Home | L | 0-2 | 0 | | |
| 27/11/1999 | Brentford | Nationwide League Division 2 | | Home | W | 2-0 | 5879 | S. Devine 44 (Pen) S. Devine 59 | |
| 30/11/1999 | Wigan Athletic | F.A. Challenge Cup | 2 Rep | Away | L | 1-2 | 3967 | A. Baird 23 | |
| 01/12/1999 | Bristol City | Avon Insurance League Cup | 1 | Home | L | 1-2 | 0 | M. Lee 86 | |
| 04/12/1999 | Burnley | Nationwide League Division 2 | | Away | L | 0-1 | 9149 | | |
| 08/12/1999 | Portsmouth | Avon Insurance Combination | | Home | L | 0-4 | 0 | | |
| 11/12/1999 | Millwall | Nationwide League Division 2 | | Home | L | 1-2 | 4777 | K. Ryan 62 | |
| 15/12/1999 | Bournemouth | Avon Insurance League Cup | 1 | Away | L | 0-5 | 0 | | |
| 17/12/1999 | Bristol City | Nationwide League Division 2 | | Away | D | 0-0 | 8195 | | |
| 26/12/1999 | Bournemouth | Nationwide League Division 2 | | Home | W | 2-1 | 5656 | S. Brown 26 S. Devine 55 | |
| 03/01/2000 | Chesterfield | Nationwide League Division 2 | | Home | W | 3-0 | 5001 | S. Devine 40 S. Devine 59 D. Bulman 90 | |
| 04/01/2000 | Chesham United | Berks & Bucks Senior Cup (from 93/94) | 3 | Home | W | 4-1 | 241 | R. Thompson 13 M. Brady 16 R. Thompson 53 R. Thompson 60 | |
| 08/01/2000 | Millwall | Nationwide League Division 2 | | Away | D | 1-1 | 8945 | S. Devine 13 | |
| 11/01/2000 | Oxford United | Auto Windscreen Shield | 2 | Away | W | 1-1 | 1797 | J. McSporran 40 | AET Oxford won 5-3 on Penalties |
| 12/01/2000 | Oxford United | Avon Insurance Combination | | Home | W | 4-2 | 0 | L. Phelan 68 I. Simpemba 72 R. Johnson 75 M. Brady 83 | |
| 15/01/2000 | Scunthorpe United | Nationwide League Division 2 | | Home | W | 2-1 | 4850 | J. Bates 30 K. Ryan 58 | |
| 18/01/2000 | Colchester United | Nationwide League Division 2 | | Away | L | 0-1 | 4075 | | |
| 22/01/2000 | Preston North End | Nationwide League Division 2 | | Away | L | 2-3 | 10969 | M. Brady 5 M. Lawrence 57 | |
| 25/01/2000 | Southend United | Avon Insurance Combination | | Away | L | 3-4 | 75 | D. Bulman 7 M. Harkin 45 D. Senda 78 | |
| 05/02/2000 | Wrexham | Nationwide League Division 2 | | Away | W | 3-1 | 2781 | M. Brady 54 D. Carroll 77 D. Senda 90 | |
| 08/02/2000 | Thatcham Town | Berks & Bucks Senior Cup (from 93/94) | 4 | Away | W | 2-0 | 467 | M. Harkin 13 L. Holsgrove 90 | |
| 12/02/2000 | Oxford United | Nationwide League Division 2 | | Home | L | 0-1 | 6200 | | |
| 19/02/2000 | Brentford | Nationwide League Division 2 | | Away | D | 0-0 | 5981 | | |
| 23/02/2000 | Bristol Rovers | Avon Insurance Combination | | Away | D | 1-1 | 0 | R. Thompson 32 | |
| 26/02/2000 | Bury | Nationwide League Division 2 | | Home | W | 3-0 | 4909 | S. Devine 40 S. Devine 57 (Pen) S. Devine 85 | |
| 01/03/2000 | Norwich City | Avon Insurance Combination | | Home | L | 0-2 | 0 | | |
| 03/03/2000 | Cardiff City | Nationwide League Division 2 | | Away | D | 2-2 | 5011 | J. McSporran 18 S. Devine 55 (Pen) | |
| 07/03/2000 | Bristol Rovers | Nationwide League Division 2 | | Away | L | 0-1 | 8053 | | |
| 08/03/2000 | Swindon Town | Avon Insurance Combination | | Away | L | 2-4 | 60 | R. Thompson 31 D. Senda 78 | |
| 11/03/2000 | Oldham Athletic | Nationwide League Division 2 | | Home | D | 0-0 | 4471 | | |
| 13/03/2000 | Colchester United | Avon Insurance Combination | | Home | L | 1-3 | 0 | D. Bulman 75 | |
| 15/03/2000 | Queens Park Rangers | Avon Insurance Combination | | Away | L | 1-7 | 120 | D. Bulman 63 | |
| 18/03/2000 | Stoke City | Nationwide League Division 2 | | Away | D | 1-1 | 9738 | J. McSporran 23 | |
| 21/03/2000 | Wigan Athletic | Nationwide League Division 2 | | Home | L | 0-2 | 3821 | | |
| 25/03/2000 | Bournemouth | Nationwide League Division 2 | | Away | L | 0-2 | 4393 | | |
| 28/03/2000 | Gillingham | Nationwide League Division 2 | | Home | W | 1-0 | 4183 | A. Baird 83 | |
| 29/03/2000 | Ipswich Town | Avon Insurance Combination | | Away | L | 0-7 | 140 | | |
| 01/04/2000 | Bristol City | Nationwide League Division 2 | | Home | L | 1-2 | 4754 | S. Devine 63 | |
| 06/04/2000 | Bristol City | Avon Insurance Combination | | Away | L | 1-2 | 0 | J. Bates 0 | |
| 08/04/2000 | Chesterfield | Nationwide League Division 2 | | Away | W | 2-1 | 2081 | K. Ryan 51 S. Devine 76 | |
| 11/04/2000 | Reading | Berks & Bucks Senior Cup (from 93/94) | S/F | Home | L | 2-4 | 0 | M. Brady 45 J. McSporran 63 | |
| 13/04/2000 | Brighton & Hove Albion | Avon Insurance Combination | | Away | D | 1-1 | 0 | M. Brady 89 | |
| 15/04/2000 | Colchester United | Nationwide League Division 2 | | Home | W | 3-0 | 4558 | K. Ryan 62 K. Ryan 67 S. Brown 90 | |
| 18/04/2000 | Bournemouth | Avon Insurance Combination | | Home | L | 1-4 | 0 | L. Holsgrove 80 | |
| 21/04/2000 | Notts County | Nationwide League Division 2 | | Home | W | 2-0 | 4369 | S. Devine 40 J. McSporran 76 | |
| 24/04/2000 | Reading | Nationwide League Division 2 | | Away | L | 1-2 | 11834 | J. McSporran 64 | |
| 26/04/2000 | Gillingham | Avon Insurance Combination | | Away | L | 0-2 | 0 | | |
| 29/04/2000 | Luton Town | Nationwide League Division 2 | | Home | L | 0-1 | 5379 | | |
| 02/05/2000 | Millwall | Avon Insurance Combination | | Away | L | 0-1 | 0 | | |
| 06/05/2000 | Cambridge United | Nationwide League Division 2 | | Away | W | 2-1 | 5335 | A. Baird 35 J. McSporran 87 | |