| Tuesday 7th May 2019 | |||||
| Chairmans Trophy Final | |||||
| Bottesford FC | 1 | 0 | Sileby Victoria | ||
|
Saturday 20th April 2019 |
|||||
| Chairmans Trophy Semi Finals | |||||
| East Leake Robins | 0 | 4 | Bottesford FC | ||
| Sileby Victoria | 3 | 2 | Wymeswold FC Reserves | ||
| Chairmans Trophy Quarter Finals | |||||
| FC Polonia | 1 | 2 | East Leake Robins | ||
| Greenhill YC Reserves | 2 | 5 | Bottesford FC | ||
| Sileby Victoria | 5 | 4 | Thringstone MW FC Reserves | ||
| Wymeswold FC Reserves | 5 | 2 | Market Bosworth | ||
| Chairmans Trophy 2018-2019 | ||||||||
| Final Group Tables | ||||||||
| GROUP A | PL | W | D | L | F | A | PTS | G/D |
| Greenhill YC Reserves | 3 | 2 | 1 | 0 | 8 | 4 | 7 | 4 |
| Market Bosworth | 3 | 2 | 0 | 1 | 7 | 6 | 6 | 1 |
| FC Coalville | 3 | 1 | 0 | 1 | 6 | 6 | 3 | 0 |
| Measham Welfare | 3 | 0 | 1 | 2 | 7 | 12 | 1 | -5 |
| GROUP B | PL | W | D | L | F | A | PTS | G/D |
| Wymeswold FC Reserves | 3 | 2 | 1 | 0 | 4 | 2 | 7 | 2 |
| Bottesford FC | 3 | 2 | 0 | 1 | 9 | 4 | 6 | 5 |
| Asfordby FC Development | 3 | 1 | 1 | 1 | 3 | 5 | 4 | -2 |
| CK Dons | 3 | 0 | 0 | 3 | 4 | 7 | 0 | -3 |
| GROUP C | PL | W | D | L | F | A | PTS | G/D |
| Sileby Victoria | 4 | 3 | 1 | 0 | 15 | 4 | 10 | 11 |
| East Leake Robins | 4 | 3 | 1 | 0 | 11 | 2 | 10 | 9 |
| Shepshed Amateurs | 4 | 2 | 0 | 2 | 15 | 9 | 6 | 6 |
| Greenhill YC ‘A’ | 4 | 1 | 0 | 3 | 7 | 26 | 3 | -19 |
| Woodhouse Imperial | 4 | 0 | 0 | 4 | 13 | 20 | 0 | -7 |
| GROUP D | PL | W | D | L | F | A | PTS | G/D |
| FC Polonia | 4 | 4 | 0 | 0 | 16 | 5 | 12 | 11 |
| Thringstone MW FC Reserves | 4 | 2 | 1 | 1 | 12 | 12 | 7 | 0 |
| Loughborough United | 4 | 2 | 1 | 1 | 9 | 10 | 7 | -1 |
| Shepshed Amateurs Reserves | 4 | 1 | 0 | 3 | 7 | 12 | 3 | -5 |
| Loughborough Emmanuel | 4 | 0 | 0 | 4 | 5 | 15 | 0 | -10 |