Results
| Date | Competition | Home | Score | Away | Attendance |
|---|
| August 7, 1999 | League Division 2 |  | AFC Bournemouth | 2-1 |  | Cambridge United | 5552 |
| August 10, 1999 | League Cup | | AFC Bournemouth | 2-0 |  | Barnet | |
| August 14, 1999 | League Division 2 |  | Bristol City | 3-1 | | AFC Bournemouth | 11315 |
| August 21, 1999 | League Division 2 | | AFC Bournemouth | 4-0 |  | Colchester United | 4508 |
| August 24, 1999 | League Cup | | Barnet | 3-2 | | AFC Bournemouth | |
| August 28, 1999 | League Division 2 |  | Scunthorpe United | 3-1 | | AFC Bournemouth | 3376 |
| August 31, 1999 | League Division 2 | | AFC Bournemouth | 1-0 |  | Luton Town | 4797 |
| September 3, 1999 | League Division 2 |  | Burnley | 2-1 | | AFC Bournemouth | 10223 |
| September 11, 1999 | League Division 2 | | AFC Bournemouth | 3-1 |  | Reading | 6007 |
| September 14, 1999 | League Cup |  | Charlton Athletic | 0-0 | | AFC Bournemouth | 10346 |
| September 18, 1999 | League Division 2 |  | Blackpool | 0-0 | | AFC Bournemouth | 4471 |
| September 21, 1999 | League Cup | | AFC Bournemouth | 0-0 | | Charlton Athletic | 4369 |
| September 25, 1999 | League Division 2 | | AFC Bournemouth | 1-1 |  | Bury | 4208 |
| October 2, 1999 | League Division 2 |  | Chesterfield | 0-1 | | AFC Bournemouth | 2775 |
| October 13, 1999 | League Cup |  | West Ham United | 2-0 | | AFC Bournemouth | 22067 |
| October 16, 1999 | League Division 2 | | AFC Bournemouth | 1-1 |  | Stoke City | 5990 |
| October 19, 1999 | League Division 2 | | AFC Bournemouth | 0-1 |  | Bristol Rovers | 5613 |
| October 23, 1999 | League Division 2 | | Bury | 2-2 | | AFC Bournemouth | 3701 |
| October 30, 1999 | FA Cup |  | Notts County | 1-1 | | AFC Bournemouth | 3674 |
| November 3, 1999 | League Division 2 |  | Preston North End | 3-0 | | AFC Bournemouth | 9630 |
| November 6, 1999 | League Division 2 | | AFC Bournemouth | 1-0 |  | Cardiff City | 4471 |
| November 9, 1999 | FA Cup | | AFC Bournemouth | 4-2 | | Notts County | 4026 |
| November 12, 1999 | League Division 2 |  | Gillingham | 4-1 | | AFC Bournemouth | 6336 |
| November 16, 1999 | League Division 2 |  | Wigan Athletic | 3-1 | | AFC Bournemouth | 4338 |
| November 20, 1999 | FA Cup | | AFC Bournemouth | 0-2 | | Bristol City | 5223 |
| November 23, 1999 | League Division 2 | | AFC Bournemouth | 4-1 |  | Brentford | 4202 |
| November 27, 1999 | League Division 2 | | AFC Bournemouth | 1-2 |  | Millwall | 5121 |
| December 4, 1999 | League Division 2 | | Cambridge United | 0-2 | | AFC Bournemouth | 3579 |
| December 11, 1999 | League Division 2 | | Notts County | 5-1 | | AFC Bournemouth | 4199 |
| December 18, 1999 | League Division 2 | | AFC Bournemouth | 4-0 |  | Oxford United | 4443 |
| December 26, 1999 | League Division 2 |  | Wycombe Wanderers | 2-1 | | AFC Bournemouth | 5656 |
| December 28, 1999 | League Division 2 | | AFC Bournemouth | 1-0 |  | Wrexham | 5394 |
| January 3, 2000 | League Division 2 |  | Oldham Athletic | 1-0 | | AFC Bournemouth | 5160 |
| January 8, 2000 | League Division 2 | | AFC Bournemouth | 1-1 | | Notts County | 4344 |
| January 11, 2000 | Auto Windscreens Shield | | AFC Bournemouth | 1-0 |  | Brighton and Hove Albion | 4325 |
| January 15, 2000 | League Division 2 | | AFC Bournemouth | 2-3 | | Bristol City | 5425 |
| January 22, 2000 | League Division 2 | | Colchester United | 3-1 | | AFC Bournemouth | 3767 |
| January 25, 2000 | Auto Windscreens Shield | | Bristol City | 1-1 | | AFC Bournemouth | 4291 |
| January 29, 2000 | League Division 2 | | AFC Bournemouth | 1-1 | | Scunthorpe United | 4802 |
| February 5, 2000 | League Division 2 | | Luton Town | 1-2 | | AFC Bournemouth | 5961 |
| February 12, 2000 | League Division 2 | | AFC Bournemouth | 0-1 | | Burnley | 5804 |
| February 19, 2000 | League Division 2 | | Millwall | 3-1 | | AFC Bournemouth | 8463 |
| February 26, 2000 | League Division 2 | | AFC Bournemouth | 2-0 | | Blackpool | 4464 |
| March 4, 2000 | League Division 2 | | Reading | 2-0 | | AFC Bournemouth | 10551 |
| March 7, 2000 | League Division 2 | | Cardiff City | 1-2 | | AFC Bournemouth | 4389 |
| March 11, 2000 | League Division 2 | | AFC Bournemouth | 0-1 | | Preston North End | 5317 |
| March 18, 2000 | League Division 2 | | Brentford | 0-2 | | AFC Bournemouth | 4578 |
| March 21, 2000 | League Division 2 | | AFC Bournemouth | 0-1 | | Gillingham | 4443 |
| March 25, 2000 | League Division 2 | | AFC Bournemouth | 2-0 | | Wycombe Wanderers | 4393 |
| April 1, 2000 | League Division 2 | | Oxford United | 1-0 | | AFC Bournemouth | 5214 |
| April 8, 2000 | League Division 2 | | AFC Bournemouth | 3-0 | | Oldham Athletic | 3808 |
| April 15, 2000 | League Division 2 | | Wrexham | 1-0 | | AFC Bournemouth | 2597 |
| April 22, 2000 | League Division 2 | | Stoke City | 1-0 | | AFC Bournemouth | 15022 |
| April 25, 2000 | League Division 2 | | AFC Bournemouth | 1-1 | | Chesterfield | 3481 |
| April 29, 2000 | League Division 2 | | Bristol Rovers | 2-2 | | AFC Bournemouth | 8847 |
| May 6, 2000 | League Division 2 | | AFC Bournemouth | 2-2 | | Wigan Athletic | 6512 |
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