| 28 Apr 2016 | Second Eleven Trophy 2016 | Middlesex Second XI v Marylebone Cricket Club Young Cricketers | Brunton Memorial Ground, Radlett | Won by 5 wkts |
| 02 Jun 2016 | Second Eleven Trophy 2016 | Middlesex Second XI v Surrey Second XI | Kenton Court Meadow, Sunbury-on-Thames | Lost by 41 runs |
| 22 Jun 2016 | Second Eleven Trophy 2016 | Essex Second XI v Middlesex Second XI | The Toby Howe Cricket Ground, Billericay | Lost by 48 runs |
| 07 Jul 2016 | Second Eleven Trophy 2016 | Middlesex Second XI v Gloucestershire Second XI | Brunton Memorial Ground, Radlett | Won by 5 wkts |
| 15 Jul 2016 | Second Eleven Trophy 2016 | Sussex Second XI v Middlesex Second XI | Spen Cama Memorial Ground, Fulking | Lost by 3 wkts |
| 12 Aug 2016 | Second Eleven Trophy 2016 | Kent Second XI v Middlesex Second XI | The Kent County Cricket Ground, Beckenham | Lost by 48 runs |
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