| 12 Jun 2000 | AON Risks Trophy 2000 | Middlesex Second XI v Northamptonshire Second XI | Corfton Road, Ealing | Lost by 10 runs |
| 19 Jun 2000 | AON Risks Trophy 2000 | Middlesex Second XI v Essex Second XI | Payne's Folly, Harrow | Won by 6 wkts |
| 29 Jun 2000 | AON Risks Trophy 2000 | Derbyshire Second XI v Middlesex Second XI | County Ground, Derby | Won by 8 wkts |
| 30 Jun 2000 | AON Risks Trophy 2000 | Northamptonshire Second XI v Middlesex Second XI | Orlingbury Road, Isham | Abandoned |
| 03 Jul 2000 | AON Risks Trophy 2000 | Middlesex Second XI v Kent Second XI | Old Deer Park, Richmond | No result |
| 06 Jul 2000 | AON Risks Trophy 2000 | Middlesex Second XI v Derbyshire Second XI | Arden Field, Finchley | Lost by 13 runs |
| 10 Jul 2000 | AON Risks Trophy 2000 | Essex Second XI v Middlesex Second XI | Ashwells Road, Brentwood | Abandoned |
| 13 Jul 2000 | AON Risks Trophy 2000 | Kent Second XI v Middlesex Second XI | St Lawrence Ground, Canterbury | Lost by 4 wkts |
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