| DIVISION FIVE | Played | |||
| Downend F | Grendel D | 3 | 3 | 9/14/99 |
| Hanham C | Yate B | 2 | 4 | 9/14/99 |
| Cabot B | Hanham B | 2.5 | 3.5 | 9/15/99 |
| Hanham B | Hanham C | 4 | 2 | 9/21/99 |
| Yate B | Clifton D | 3 | 3 | 9/21/99 |
| Cabot B | Downend F | 2 | 4 | 9/22/99 |
| Harambee B | Yate B | 6 | 0 | 9/30/99 |
| Hanham C | Clifton D | 3 | 3 | 10/5/99 |
| Yate B | Cabot B | 3.5 | 2.5 | 10/5/99 |
| Grendel D | Harambee B | 5 | 1 | 10/6/99 |
| Hanham B | University B | 3.5 | 2.5 | 10/12/99 |
| Hanham B | Harambee B | 3 | 3 | 10/19/99 |
| Clifton D | Downend F | 2.5 | 2.5 | 10/21/99 |
| University B | Cabot B | 2 | 4 | 10/21/99 |
| Hanham C | University B | 2.5 | 3.5 | 10/26/99 |
| Yate B | Grendel D | 1.5 | 4.5 | 10/26/99 |
| Cabot B | Harambee B | 4.5 | 1.5 | 10/27/99 |
| Yate B | Hanham B | 1.5 | 4.5 | 11/2/99 |
| Harambee B | Hanham C | 3 | 3 | 11/4/99 |
| University B | Clifton D | 1.5 | 4.5 | 11/4/99 |
| Downend F | University B | 2.5 | 3.5 | 11/9/99 |
| Grendel D | Hanham B | 3 | 3 | 11/10/99 |
| Clifton D | Cabot B | 3.5 | 2.5 | 11/11/99 |
| Downend F | Yate B | 3 | 3 | 11/23/99 |
| Cabot B | Hanham C | 4 | 2 | 11/24/99 |
| Clifton D | Harambee B | 4.5 | 1.5 | 1/20/00 |
| University B | Grendel D | 5 | 1 | 11/25/99 |
| Hanham B | Downend F | 3.5 | 2.5 | 11/30/99 |
| Grendel D | Cabot B | 4.5 | 1.5 | 12/1/99 |
| Harambee B | University B | 2.5 | 3.5 | 12/2/99 |
| Hanham C | Grendel D | 0 | 6 | 12/7/99 |
| Clifton D | Hanham B | 3.5 | 2.5 | 12/9/99 |
| Harambee B | Downend F | 3 | 3 | 12/9/99 |
| University B | Yate B | 2.5 | 3.5 | 12/9/99 |
| Downend F | Hanham C | 4 | 2 | 12/14/99 |
| Grendel D | Clifton D | 2.5 | 3.5 | 12/15/99 |
| Downend F | Clifton D | 3 | 3 | 1/4/00 |
| Hanham C | Cabot B | 2.5 | 3.5 | 1/4/00 |
| Grendel D | Yate B | 2.5 | 3.5 | 1/5/00 |
| Harambee B | Hanham B | 1 | 5 | 1/6/00 |
| Yate B | Downend F | 5 | 1 | 1/11/00 |
| University B | Hanham B | 3.5 | 2.5 | 3/26/00 |
| Hanham C | Downend F | 2.5 | 3.5 | 1/18/00 |
| Hanham B | Clifton D | 1.5 | 4.5 | 1/25/00 |
| Cabot B | University B | 4 | 2 | 1/26/00 |
| Yate B | Hanham C | 4.5 | 1.5 | 2/1/00 |
| Grendel D | Downend F | 3 | 3 | 2/2/00 |
| Clifton D | University B | 3 | 3 | 2/3/00 |
| Harambee B | Cabot B | 2.5 | 3.5 | 2/3/00 |
| Hanham C | Hanham B | 1 | 4 | 2/15/00 |
| Yate B | University B | 4 | 2 | 2/15/00 |
| Hanham B | Grendel D | 4.5 | 1.5 | 2/22/00 |
| Yate B | Harambee B | 4 | 2 | 2/22/00 |
| Cabot B | Clifton D | 3.5 | 2.5 | 3/1/00 |
| University B | Downend F | 5 | 1 | 2/24/00 |
| Cabot B | Grendel D | 2 | 4 | 3/8/00 |
| Clifton D | Hanham C | 3.5 | 2.5 | 3/9/00 |
| University B | Harambee B | 0 | 6 | 3/9/00 |
| Downend F | Cabot B | 0.5 | 5.5 | 3/14/00 |
| Hanham B | Yate B | 4 | 2 | 3/14/00 |
| Harambee B | Grendel D | 5 | 1 | 3/16/00 |
| University B | Hanham C | 4 | 2 | 3/16/00 |
| Grendel D | University B | 5 | 1 | 3/22/00 |
| Harambee B | Clifton D | 2.5 | 3.5 | 3/23/00 |
| Downend F | Harambee B | 3 | 3 | 4/4/00 |
| Hanham B | Cabot B | 2.5 | 3.5 | 4/4/00 |
| Grendel D | Hanham C | 4.5 | 1.5 | 4/5/00 |
| Clifton D | Yate B | 3.5 | 2.5 | 4/6/00 |
| Downend F | Hanham B | 0 | 6 | 4/18/00 |
| Cabot B | Yate B | 1 | 5 | 4/19/00 |
| Hanham C | Harambee B | 4 | 2 | 4/25/00 |
| Clifton D | Grendel D | 4 | 2 | 4/13/00 |
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