| Thursday 4th April 2019 | |||||
| Cobbin Trophy Semi Final | |||||
| CT01 | Greenhill YC | 3 | 2 | Woodhouse Imperial | |
| Thursday 11th April 2019 | |||||
| Cobbin Trophy Semi Final | at Loughborough Dynamo FC KO 7.30pm | ||||
| CT2 | Rothley Imperial | v | Falcons FC | ||
| Quarter Finals | ||||
| Falcons FC | 6 | 0 | Bottesford FC | |
| Greenhill YC | 2 | 1 | Sporting Markfield | |
| Kegworth Imperial | 2 | 3 | Woodhouse Imperial | |
| Sutton Bonington | 2 | 4 | Rothley Imperial |
| 2nd Round | ||||
| Belton Villa | 3 | aet | 4 | Kegworth Imperial |
| Birstall Old Boys | 1 | 6 | Sutton Bonington | |
| Bottesford FC | 8 | 0 | Quorn Rangers FC | |
| FC Coalville | 2 | 3 | Woodhouse Imperial | |
| FC Polonia | 0 | 8 | Falcons FC | |
| Mountsorrel Amateurs | 2 | 4 | Greenhill YC | |
| Shepshed Amateurs | 2 | 3 | Rothley Imperial | |
| Sporting Markfield | 3 | 0 | Thorpe Acre |
| 1st Round | ||||
| CK Dons | 2 | 4 | Bottesford FC | |
| Falcons FC | 9 | 1 | East Leake Robins | |
| FC Coalville | 7 | 4 | Ravenstone United | |
| FC Polonia | 4 | 2 | Loughborough United | |
| Kegworth Imperial | H | W | Shelthorpe Dynamo | |
| Market Bosworth | 2 | 6 | Greenhill YC | |
| Measham Welfare | 1 | 8 | Sporting Markfield | |
| Midland Red | A | W | Woodhouse Imperial | |
| Mountsorrel Amateurs | H | W | Cossington Saints | |
| Mountsorrel FC | 1 | 4 | Belton Villa | |
| Rothley Imperial | H | W | Loughborough Emmanuel | |
| Shepshed Amateurs | 5 | 0 | Sileby Victoria | |