| Leicester Senior | ||||
| Date | Home | H | A | Away |
| 06/05/2000 | Ellistown | 2 | 1 | Holwell Sports |
| 06/05/2000 | Friar Lane OB | 0 | 7 | Downes Sports |
| 04/05/2000 | Cottesmore Amateurs | 2 | 5 | Quorn |
| 29/04/2000 | Anstey Nomads | 4 | 2 | Thringstone United |
| 29/04/2000 | Aylestone Park OB | 1 | 3 | Highfield Rangers |
| 29/04/2000 | Birstall United | 3 | 3 | Friar Lane OB |
| 29/04/2000 | Downes Sports | 0 | 0 | Coalville Town |
| 29/04/2000 | Holwell Sports | 1 | 2 | Thurmaston Town (P) |
| 29/04/2000 | Kirby Muxloe SC | 3 | 1 | Lutterworth Town |
| 29/04/2000 | Quorn | 1 | 2 | Barrow Town |
| 29/04/2000 | St Andrews SC | 3 | 1 | Ibstock Welfare |
| 27/04/2000 | Anstey Nomads | 0 | 5 | Barrow Town |
| 22/04/2000 | Highfield Rangers | 1 | 1 | Ellistown |
| 22/04/2000 | Ibstock Welfare | 3 | 1 | Aylestone Park OB |
| 22/04/2000 | Thringstone United | 3 | 2 | Birstall United |
| 22/04/2000 | Thurmaston Town (P) | 0 | 1 | Kirby Muxloe SC |
| 17/04/2000 | Anstey Nomads | 1 | 2 | Coalville Town |
| 15/04/2000 | Aylestone Park OB | 4 | 1 | Lutterworth Town |
| 15/04/2000 | Barrow Town | 2 | 3 | Cottesmore Amateurs |
| 15/04/2000 | Birstall United | 1 | 2 | Anstey Nomads |
| 15/04/2000 | Holwell Sports | 2 | 2 | Friar Lane OB |
| 15/04/2000 | Ibstock Welfare | 0 | 3 | Ellistown |
| 15/04/2000 | Kirby Muxloe SC | 4 | 3 | Coalville Town |
| 15/04/2000 | Quorn | 2 | 4 | Highfield Rangers |
| 15/04/2000 | St Andrews SC | 2 | 0 | Thurmaston Town (P) |
| 10/04/2000 | Anstey Nomads | 2 | 2 | Holwell Sports |
| 10/04/2000 | Highfield Rangers | 1 | 1 | Birstall United |
| 10/04/2000 | Lutterworth Town | 3 | 1 | Aylestone Park OB |
| 08/04/2000 | Anstey Nomads | 4 | 3 | Cottesmore Amateurs |
| 08/04/2000 | Birstall United | 1 | 3 | Downes Sports |
| 08/04/2000 | Coalville Town | 0 | 1 | St Andrews SC |
| 08/04/2000 | Friar Lane OB | 1 | 6 | Kirby Muxloe SC |
| 08/04/2000 | Highfield Rangers | 4 | 1 | Barrow Town |
| 08/04/2000 | Ibstock Welfare | 2 | 1 | Quorn |
| 08/04/2000 | Lutterworth Town | 0 | 2 | Ellistown |
| 08/04/2000 | Thringstone United | 1 | 1 | Holwell Sports |
| 08/04/2000 | Thurmaston Town (P) | 4 | 1 | Aylestone Park OB |
| 03/04/2000 | Downes Sports | 1 | 0 | Holwell Sports |
| 01/04/2000 | Aylestone Park OB | 2 | 0 | Coalville Town |
| 01/04/2000 | Barrow Town | 1 | 0 | Ibstock Welfare |
| 01/04/2000 | Cottesmore Amateurs | 0 | 3 | Highfield Rangers |
| 01/04/2000 | Downes Sports | 2 | 0 | Anstey Nomads |
| 01/04/2000 | Ellistown | 1 | 6 | Thurmaston Town (P) |
| 01/04/2000 | Holwell Sports | 0 | 0 | Birstall United |
| 01/04/2000 | Kirby Muxloe SC | 1 | 0 | Thringstone United |
| 01/04/2000 | Quorn | 1 | 0 | Lutterworth Town |
| 01/04/2000 | St Andrews SC | 1 | 1 | Friar Lane OB |
| 28/03/2000 | Cottesmore Amateurs | 1 | 3 | Anstey Nomads |
| 28/03/2000 | Ibstock Welfare | 0 | 3 | Highfield Rangers |
| 28/03/2000 | Lutterworth Town | 0 | 4 | Thurmaston Town (P) |
| 25/03/2000 | Anstey Nomads | 0 | 0 | Highfield Rangers |
| 25/03/2000 | Birstall United | 3 | 4 | Kirby Muxloe SC |
| 25/03/2000 | Friar Lane OB | 1 | 1 | Aylestone Park OB |
| 25/03/2000 | Ibstock Welfare | 2 | 2 | Cottesmore Amateurs |
| 25/03/2000 | Lutterworth Town | 2 | 1 | Barrow Town |
| 25/03/2000 | Thringstone United | 0 | 5 | St Andrews SC |
| 25/03/2000 | Thurmaston Town (P) | 0 | 1 | Quorn |
| 21/03/2000 | Coalville Town | 2 | 0 | Ellistown |
| 21/03/2000 | Ibstock Welfare | 1 | 1 | Birstall United |
| 18/03/2000 | Aylestone Park OB | 3 | 0 | Thringstone United |
| 18/03/2000 | Barrow Town | 2 | 1 | Thurmaston Town (P) |
| 18/03/2000 | Cottesmore Amateurs | 1 | 1 | Lutterworth Town |
| 18/03/2000 | Ellistown | 0 | 0 | Friar Lane OB |
| 18/03/2000 | Highfield Rangers | 0 | 1 | Ibstock Welfare |
| 18/03/2000 | Holwell Sports | 1 | 0 | Anstey Nomads |
| 18/03/2000 | Kirby Muxloe SC | 1 | 0 | Downes Sports |
| 18/03/2000 | Quorn | 3 | 3 | Coalville Town |
| 18/03/2000 | St Andrews SC | 2 | 1 | Birstall United |
| 14/03/2000 | Coalville Town | 0 | 1 | Birstall United |
| 14/03/2000 | Lutterworth Town | 0 | 2 | Holwell Sports |
| 11/03/2000 | Anstey Nomads | 1 | 1 | Ibstock Welfare |
| 11/03/2000 | Birstall United | 1 | 1 | Aylestone Park OB |
| 11/03/2000 | Coalville Town | 0 | 3 | Barrow Town |
| 11/03/2000 | Downes Sports | 0 | 3 | St Andrews SC |
| 11/03/2000 | Friar Lane OB | 2 | 0 | Quorn |
| 11/03/2000 | Holwell Sports | 0 | 2 | Kirby Muxloe SC |
| 11/03/2000 | Lutterworth Town | 0 | 3 | Highfield Rangers |
| 11/03/2000 | Thringstone United | 1 | 2 | Ellistown |
| 11/03/2000 | Thurmaston Town (P) | 2 | 2 | Cottesmore Amateurs |
| 04/03/2000 | Aylestone Park OB | 2 | 3 | Downes Sports |
| 04/03/2000 | Barrow Town | 2 | 1 | Friar Lane OB |
| 04/03/2000 | Cottesmore Amateurs | 0 | 2 | Coalville Town |
| 04/03/2000 | Ellistown | 1 | 1 | Birstall United |
| 04/03/2000 | Highfield Rangers | 1 | 0 | Thurmaston Town (P) |
| 04/03/2000 | Ibstock Welfare | 1 | 1 | Lutterworth Town |
| 04/03/2000 | Kirby Muxloe SC | 1 | 2 | Anstey Nomads |
| 04/03/2000 | Quorn | 2 | 2 | Thringstone United |
| 04/03/2000 | St Andrews SC | 3 | 0 | Holwell Sports |
| 26/02/2000 | Birstall United | 0 | 3 | Quorn |
| 26/02/2000 | Coalville Town | 0 | 1 | Highfield Rangers |
| 26/02/2000 | Downes Sports | 1 | 1 | Ellistown |
| 26/02/2000 | Friar Lane OB | 1 | 6 | Cottesmore Amateurs |
| 26/02/2000 | Holwell Sports | 4 | 1 | Aylestone Park OB |
| 26/02/2000 | Kirby Muxloe SC | 1 | 0 | St Andrews SC |
| 26/02/2000 | Thringstone United | 2 | 3 | Barrow Town |
| 26/02/2000 | Thurmaston Town (P) | 0 | 1 | Ibstock Welfare |
| 19/02/2000 | Aylestone Park OB | 1 | 2 | Kirby Muxloe SC |
| 19/02/2000 | Barrow Town | 3 | 3 | Birstall United |
| 19/02/2000 | Cottesmore Amateurs | 2 | 2 | Thringstone United |
| 19/02/2000 | Highfield Rangers | 3 | 2 | Friar Lane OB |
| 19/02/2000 | Ibstock Welfare | 3 | 0 | Coalville Town |
| 19/02/2000 | St Andrews SC | 5 | 0 | Anstey Nomads |
| 16/02/2000 | Cottesmore Amateurs | 3 | 1 | Barrow Town |
| 15/02/2000 | Anstey Nomads | 4 | 0 | Birstall United |
| 15/02/2000 | Ibstock Welfare | 1 | 5 | Holwell Sports |
| 15/02/2000 | Lutterworth Town | 2 | 5 | Quorn |
| 15/02/2000 | Thurmaston Town (P) | 2 | 2 | Downes Sports |
| 12/02/2000 | Anstey Nomads | 1 | 2 | Thurmaston Town (P) |
| 12/02/2000 | Birstall United | 2 | 2 | Cottesmore Amateurs |
| 12/02/2000 | Coalville Town | 0 | 1 | Lutterworth Town |
| 12/02/2000 | Downes Sports | 2 | 1 | Barrow Town |
| 12/02/2000 | Friar Lane OB | 2 | 3 | Ibstock Welfare |
| 12/02/2000 | Holwell Sports | 0 | 1 | Quorn |
| 12/02/2000 | Kirby Muxloe SC | 5 | 1 | Ellistown |
| 12/02/2000 | St Andrews SC | 0 | 0 | Aylestone Park OB |
| 12/02/2000 | Thringstone United | 0 | 1 | Highfield Rangers |
| 08/02/2000 | Coalville Town | 1 | 1 | Kirby Muxloe SC |
| 08/02/2000 | Highfield Rangers | 5 | 0 | Cottesmore Amateurs |
| 08/02/2000 | Quorn | 4 | 2 | Anstey Nomads |
| 08/02/2000 | Thurmaston Town (P) | 5 | 2 | Ellistown |
| 05/02/2000 | Aylestone Park OB | 1 | 1 | Anstey Nomads |
| 05/02/2000 | Barrow Town | 1 | 1 | Holwell Sports |
| 05/02/2000 | Cottesmore Amateurs | 2 | 4 | Downes Sports |
| 05/02/2000 | Ellistown | 1 | 1 | St Andrews SC |
| 05/02/2000 | Ibstock Welfare | 1 | 2 | Thringstone United |
| 05/02/2000 | Lutterworth Town | 0 | 3 | Friar Lane OB |
| 05/02/2000 | Quorn | 2 | 0 | Kirby Muxloe SC |
| 05/02/2000 | Thurmaston Town (P) | 1 | 1 | Coalville Town |
| 01/02/2000 | Ellistown | 1 | 5 | Quorn |
| 29/01/2000 | Anstey Nomads | 2 | 0 | Lutterworth Town |
| 29/01/2000 | Aylestone Park OB | 1 | 1 | Ellistown |
| 29/01/2000 | Downes Sports | 1 | 0 | Highfield Rangers |
| 29/01/2000 | Friar Lane OB | 1 | 1 | Thurmaston Town (P) |
| 29/01/2000 | Holwell Sports | 2 | 6 | Cottesmore Amateurs |
| 29/01/2000 | Kirby Muxloe SC | 2 | 2 | Barrow Town |
| 29/01/2000 | St Andrews SC | 3 | 0 | Quorn |
| 29/01/2000 | Thringstone United | 1 | 1 | Coalville Town |
| 25/01/2000 | Birstall United | 1 | 3 | Ibstock Welfare |
| 25/01/2000 | Friar Lane OB | 2 | 4 | Holwell Sports |
| 25/01/2000 | Thurmaston Town (P) | 3 | 5 | St Andrews SC |
| 22/01/2000 | Barrow Town | 0 | 4 | St Andrews SC |
| 22/01/2000 | Coalville Town | 2 | 1 | Friar Lane OB |
| 22/01/2000 | Ellistown | 1 | 2 | Anstey Nomads |
| 22/01/2000 | Highfield Rangers | 2 | 2 | Holwell Sports |
| 22/01/2000 | Ibstock Welfare | 1 | 0 | Downes Sports |
| 22/01/2000 | Lutterworth Town | 1 | 2 | Birstall United |
| 22/01/2000 | Quorn | 1 | 1 | Aylestone Park OB |
| 22/01/2000 | Thurmaston Town (P) | 1 | 2 | Thringstone United |
| 15/01/2000 | Anstey Nomads | 6 | 1 | Friar Lane OB |
| 15/01/2000 | Aylestone Park OB | 2 | 2 | Barrow Town |
| 15/01/2000 | Birstall United | 3 | 3 | Thurmaston Town (P) |
| 15/01/2000 | Downes Sports | 10 | 2 | Lutterworth Town |
| 15/01/2000 | Ellistown | 0 | 1 | Ibstock Welfare |
| 15/01/2000 | Holwell Sports | 1 | 1 | Coalville Town |
| 15/01/2000 | Kirby Muxloe SC | 1 | 2 | Highfield Rangers |
| 15/01/2000 | St Andrews SC | 7 | 0 | Cottesmore Amateurs |
| 15/01/2000 | Thringstone United | 3 | 1 | Quorn |
| 08/01/2000 | Barrow Town | 1 | 2 | Ellistown |
| 08/01/2000 | Cottesmore Amateurs | 0 | 2 | Aylestone Park OB |
| 08/01/2000 | Friar Lane OB | 0 | 2 | Thringstone United |
| 08/01/2000 | Highfield Rangers | 0 | 3 | St Andrews SC |
| 08/01/2000 | Kirby Muxloe SC | 2 | 2 | Ibstock Welfare |
| 08/01/2000 | Quorn | 3 | 1 | Downes Sports |
| 27/12/1999 | Barrow Town | 0 | 3 | Quorn |
| 27/12/1999 | Coalville Town | 0 | 0 | Downes Sports |
| 27/12/1999 | Friar Lane OB | 2 | 0 | Birstall United |
| 27/12/1999 | Highfield Rangers | 3 | 0 | Aylestone Park OB |
| 27/12/1999 | Ibstock Welfare | 3 | 1 | St Andrews SC |
| 27/12/1999 | Lutterworth Town | 1 | 4 | Kirby Muxloe SC |
| 27/12/1999 | Thringstone United | 3 | 1 | Anstey Nomads |
| 27/12/1999 | Thurmaston Town (P) | 1 | 1 | Holwell Sports |
| 18/12/1999 | Aylestone Park OB | 3 | 1 | Ibstock Welfare |
| 18/12/1999 | Barrow Town | 1 | 1 | Anstey Nomads |
| 18/12/1999 | Birstall United | 2 | 1 | Thringstone United |
| 18/12/1999 | Downes Sports | 2 | 2 | Friar Lane OB |
| 18/12/1999 | Ellistown | 1 | 5 | Highfield Rangers |
| 18/12/1999 | Kirby Muxloe SC | 5 | 2 | Thurmaston Town (P) |
| 18/12/1999 | Quorn | 2 | 2 | Cottesmore Amateurs |
| 18/12/1999 | St Andrews SC | 2 | 2 | Lutterworth Town |
| 11/12/1999 | Highfield Rangers | 1 | 1 | Quorn |
| 11/12/1999 | Thringstone United | 1 | 0 | Downes Sports |
| 07/12/1999 | Anstey Nomads | 1 | 5 | Kirby Muxloe SC |
| 07/12/1999 | Coalville Town | 0 | 1 | Quorn |
| 07/12/1999 | Friar Lane OB | 1 | 4 | St Andrews SC |
| 07/12/1999 | Lutterworth Town | 0 | 1 | Ibstock Welfare |
| 04/12/1999 | Aylestone Park OB | 1 | 2 | Thurmaston Town (P) |
| 04/12/1999 | Barrow Town | 1 | 4 | Highfield Rangers |
| 04/12/1999 | Downes Sports | 4 | 1 | Birstall United |
| 04/12/1999 | Ellistown | 1 | 4 | Lutterworth Town |
| 04/12/1999 | Holwell Sports | 1 | 7 | Thringstone United |
| 04/12/1999 | Kirby Muxloe SC | 1 | 3 | Friar Lane OB |
| 04/12/1999 | Quorn | 3 | 1 | Ibstock Welfare |
| 04/12/1999 | St Andrews SC | 4 | 0 | Coalville Town |
| 27/11/1999 | Cottesmore Amateurs | 1 | 1 | Kirby Muxloe SC |
| 27/11/1999 | Downes Sports | 2 | 2 | Thringstone United |
| 27/11/1999 | Friar Lane OB | 2 | 1 | Barrow Town |
| 20/11/1999 | Aylestone Park OB | 0 | 2 | Friar Lane OB |
| 20/11/1999 | Barrow Town | 0 | 1 | Lutterworth Town |
| 20/11/1999 | Cottesmore Amateurs | 1 | 6 | Ibstock Welfare |
| 20/11/1999 | Ellistown | 0 | 1 | Coalville Town |
| 20/11/1999 | Highfield Rangers | 3 | 0 | Anstey Nomads |
| 20/11/1999 | Holwell Sports | 1 | 1 | Downes Sports |
| 20/11/1999 | Kirby Muxloe SC | 0 | 0 | Birstall United |
| 20/11/1999 | Quorn | 2 | 1 | Thurmaston Town (P) |
| 20/11/1999 | St Andrews SC | 1 | 1 | Thringstone United |
| 16/11/1999 | Ibstock Welfare | 4 | 1 | Kirby Muxloe SC |
| 13/11/1999 | Coalville Town | 3 | 2 | Holwell Sports |
| 13/11/1999 | Downes Sports | 1 | 0 | Kirby Muxloe SC |
| 13/11/1999 | Friar Lane OB | 10 | 0 | Ellistown |
| 13/11/1999 | Lutterworth Town | 3 | 4 | Cottesmore Amateurs |
| 13/11/1999 | Thringstone United | 3 | 1 | Aylestone Park OB |
| 13/11/1999 | Thurmaston Town (P) | 1 | 1 | Barrow Town |
| 11/11/1999 | Birstall United | 2 | 1 | St Andrews SC |
| 06/11/1999 | Aylestone Park OB | 3 | 2 | Birstall United |
| 06/11/1999 | Barrow Town | 1 | 1 | Coalville Town |
| 06/11/1999 | Cottesmore Amateurs | 5 | 3 | Thurmaston Town (P) |
| 06/11/1999 | Ellistown | 0 | 6 | Thringstone United |
| 06/11/1999 | Highfield Rangers | 2 | 0 | Lutterworth Town |
| 06/11/1999 | Ibstock Welfare | 3 | 1 | Anstey Nomads |
| 06/11/1999 | Kirby Muxloe SC | 3 | 1 | Holwell Sports |
| 06/11/1999 | Quorn | 2 | 3 | Friar Lane OB |
| 06/11/1999 | St Andrews SC | 1 | 2 | Downes Sports |
| 02/11/1999 | Cottesmore Amateurs | 1 | 2 | Birstall United |
| 02/11/1999 | Thurmaston Town (P) | 1 | 0 | Anstey Nomads |
| 30/10/1999 | Anstey Nomads | 1 | 2 | Downes Sports |
| 30/10/1999 | Birstall United | 1 | 0 | Holwell Sports |
| 30/10/1999 | Coalville Town | 2 | 3 | Aylestone Park OB |
| 30/10/1999 | Ellistown | 2 | 10 | Cottesmore Amateurs |
| 30/10/1999 | Ibstock Welfare | 3 | 1 | Barrow Town |
| 30/10/1999 | Lutterworth Town | 1 | 7 | St Andrews SC |
| 30/10/1999 | Thringstone United | 2 | 1 | Kirby Muxloe SC |
| 23/10/1999 | Birstall United | 3 | 0 | Ellistown |
| 23/10/1999 | Coalville Town | 6 | 2 | Cottesmore Amateurs |
| 23/10/1999 | Downes Sports | 2 | 0 | Aylestone Park OB |
| 23/10/1999 | Holwell Sports | 3 | 3 | St Andrews SC |
| 23/10/1999 | Thringstone United | 3 | 1 | Lutterworth Town |
| 23/10/1999 | Thurmaston Town (P) | 0 | 0 | Highfield Rangers |
| 16/10/1999 | Aylestone Park OB | 2 | 4 | Holwell Sports |
| 16/10/1999 | Barrow Town | 1 | 1 | Thringstone United |
| 16/10/1999 | Cottesmore Amateurs | 2 | 2 | Friar Lane OB |
| 16/10/1999 | Ellistown | 0 | 6 | Downes Sports |
| 16/10/1999 | Highfield Rangers | 3 | 0 | Coalville Town |
| 16/10/1999 | Ibstock Welfare | 1 | 2 | Thurmaston Town (P) |
| 16/10/1999 | Lutterworth Town | 1 | 1 | Anstey Nomads |
| 16/10/1999 | Quorn | 1 | 0 | Birstall United |
| 16/10/1999 | St Andrews SC | 0 | 0 | Kirby Muxloe SC |
| 09/10/1999 | Anstey Nomads | 0 | 4 | St Andrews SC |
| 09/10/1999 | Birstall United | 1 | 2 | Barrow Town |
| 09/10/1999 | Coalville Town | 3 | 0 | Ibstock Welfare |
| 09/10/1999 | Downes Sports | 1 | 2 | Quorn |
| 09/10/1999 | Friar Lane OB | 0 | 4 | Highfield Rangers |
| 09/10/1999 | Holwell Sports | 4 | 1 | Ellistown |
| 09/10/1999 | Kirby Muxloe SC | 3 | 2 | Aylestone Park OB |
| 09/10/1999 | Thringstone United | 2 | 0 | Cottesmore Amateurs |
| 09/10/1999 | Thurmaston Town (P) | 3 | 1 | Lutterworth Town |
| 05/10/1999 | Ibstock Welfare | 2 | 3 | Friar Lane OB |
| 25/09/1999 | Cottesmore Amateurs | 7 | 0 | Ellistown |
| 25/09/1999 | Highfield Rangers | 4 | 3 | Thringstone United |
| 25/09/1999 | Lutterworth Town | 0 | 2 | Coalville Town |
| 18/09/1999 | Anstey Nomads | 0 | 1 | Aylestone Park OB |
| 18/09/1999 | Birstall United | 0 | 2 | Highfield Rangers |
| 18/09/1999 | Coalville Town | 2 | 2 | Thurmaston Town (P) |
| 18/09/1999 | Downes Sports | 2 | 1 | Cottesmore Amateurs |
| 18/09/1999 | Friar Lane OB | 6 | 1 | Lutterworth Town |
| 18/09/1999 | Holwell Sports | 2 | 2 | Barrow Town |
| 18/09/1999 | Kirby Muxloe SC | 0 | 2 | Quorn |
| 18/09/1999 | St Andrews SC | 2 | 1 | Ellistown |
| 18/09/1999 | Thringstone United | 3 | 4 | Ibstock Welfare |
| 11/09/1999 | Barrow Town | 0 | 1 | Kirby Muxloe SC |
| 11/09/1999 | Coalville Town | 2 | 1 | Anstey Nomads |
| 11/09/1999 | Ellistown | 2 | 1 | Aylestone Park OB |
| 11/09/1999 | Lutterworth Town | 3 | 2 | Thringstone United |
| 11/09/1999 | Thurmaston Town (P) | 1 | 0 | Friar Lane OB |
| 06/09/1999 | Aylestone Park OB | 0 | 7 | St Andrews SC |
| 06/09/1999 | Barrow Town | 2 | 4 | Downes Sports |
| 06/09/1999 | Quorn | 0 | 1 | Holwell Sports |
| 04/09/1999 | Anstey Nomads | 5 | 2 | Ellistown |
| 04/09/1999 | Aylestone Park OB | 1 | 1 | Quorn |
| 04/09/1999 | Birstall United | 1 | 0 | Lutterworth Town |
| 04/09/1999 | Downes Sports | 0 | 0 | Ibstock Welfare |
| 04/09/1999 | Friar Lane OB | 2 | 1 | Coalville Town |
| 04/09/1999 | Holwell Sports | 0 | 6 | Highfield Rangers |
| 04/09/1999 | Kirby Muxloe SC | 5 | 0 | Cottesmore Amateurs |
| 04/09/1999 | St Andrews SC | 5 | 2 | Barrow Town |
| 04/09/1999 | Thringstone United | 1 | 0 | Thurmaston Town (P) |
| 31/08/1999 | Cottesmore Amateurs | 3 | 5 | Holwell Sports |
| 31/08/1999 | Ellistown | 0 | 4 | Kirby Muxloe SC |
| 31/08/1999 | Highfield Rangers | 2 | 2 | Downes Sports |
| 31/08/1999 | Quorn | 2 | 2 | St Andrews SC |
| 28/08/1999 | Barrow Town | 5 | 1 | Aylestone Park OB |
| 28/08/1999 | Coalville Town | 2 | 0 | Thringstone United |
| 28/08/1999 | Cottesmore Amateurs | 2 | 2 | St Andrews SC |
| 28/08/1999 | Friar Lane OB | 2 | 1 | Anstey Nomads |
| 28/08/1999 | Highfield Rangers | 3 | 1 | Kirby Muxloe SC |
| 28/08/1999 | Holwell Sports | 2 | 1 | Ibstock Welfare |
| 28/08/1999 | Lutterworth Town | 3 | 4 | Downes Sports |
| 28/08/1999 | Quorn | 2 | 0 | Ellistown |
| 28/08/1999 | Thurmaston Town (P) | 1 | 2 | Birstall United |
| 21/08/1999 | Anstey Nomads | 1 | 4 | Quorn |
| 21/08/1999 | Aylestone Park OB | 3 | 3 | Cottesmore Amateurs |
| 21/08/1999 | Birstall United | 2 | 2 | Coalville Town |
| 21/08/1999 | Downes Sports | 1 | 3 | Thurmaston Town (P) |
| 21/08/1999 | Ellistown | 0 | 5 | Barrow Town |
| 21/08/1999 | Holwell Sports | 2 | 1 | Lutterworth Town |
| 21/08/1999 | St Andrews SC | 3 | 0 | Highfield Rangers |
| 21/08/1999 | Thringstone United | 0 | 7 | Friar Lane OB |