| 26 Apr 1999 | South West Zone | Gloucestershire Second XI v Glamorgan Second XI | Seat Unique Stadium, Bristol | Results |
| 10 May 1999 | South West Zone | Hampshire Second XI v Glamorgan Second XI | United Services Ground, Portsmouth | Results |
| 24 May 1999 | South West Zone | Glamorgan Second XI v Gloucestershire Second XI | Sophia Gardens, Cardiff | Results |
| 24 May 1999 | South East Zone | Marylebone Cricket Club Young Cricketers v Essex Second XI | Shenley Sports Ground, Shenley | Results |
| 24 May 1999 | North Zone | Yorkshire Second XI v Derbyshire Second XI | Town Fields, Doncaster | Results |
| 25 May 1999 | Central Zone | Minor Counties Under-25s v Middlesex Second XI | Campbell Park, Milton Keynes | Results |
| 28 May 1999 | Central Zone | Warwickshire Second XI v Minor Counties Under-25s | Tippett's Field, Solihull | Results |
| 31 May 1999 | North Zone | Derbyshire Second XI v Yorkshire Second XI | Eyes Meadow, Duffield | Results |
| 31 May 1999 | South West Zone | Worcestershire Second XI v Gloucestershire Second XI | Visit Worcestershire New Road, Worcester | Results |
| 01 Jun 1999 | South East Zone | Essex Second XI v Marylebone Cricket Club Young Cricketers | Anglo-American Playing Fields, Saffron Walden | Results |
| 07 Jun 1999 | Central Zone | Minor Counties Under-25s v Northamptonshire Second XI | Lancot Park, Totternhoe | Results |
| 07 Jun 1999 | South West Zone | Somerset Second XI v Gloucestershire Second XI | Recreation Ground, Bath | Results |
| 08 Jun 1999 | Central Zone | Minor Counties Under-25s v Warwickshire Second XI | White Post Road, Bodicote | Results |
| 14 Jun 1999 | South West Zone | Gloucestershire Second XI v Hampshire Second XI | North Park, Cheltenham | Results |
| 14 Jun 1999 | South East Zone | Marylebone Cricket Club Young Cricketers v Surrey Second XI | Shenley Sports Ground, Shenley | Results |
| 14 Jun 1999 | Central Zone | Middlesex Second XI v Northamptonshire Second XI | Payne's Folly, Harrow | Results |
| 15 Jun 1999 | Central Zone | Middlesex Second XI v Minor Counties Under-25s | Payne's Folly, Harrow | Results |
| 21 Jun 1999 | South West Zone | Gloucestershire Second XI v Worcestershire Second XI | Seat Unique Stadium, Bristol | Results |
| 25 Jun 1999 | South East Zone | Marylebone Cricket Club Young Cricketers v Sussex Second XI | Shenley Sports Ground, Shenley | Results |
| 25 Jun 1999 | North Zone | Yorkshire Second XI v Lancashire Second XI | Centre Vale, Todmorden | Results |
| 28 Jun 1999 | South East Zone | Essex Second XI v Surrey Second XI | The Cloud County Ground, Chelmsford | Results |
| 28 Jun 1999 | South West Zone | Hampshire Second XI v Somerset Second XI | County Ground, Southampton | Results |
| 28 Jun 1999 | North Zone | Lancashire Second XI v Durham Second XI | Broadwaters, Fleetwood | Results |
| 28 Jun 1999 | Central Zone | Northamptonshire Second XI v Leicestershire Second XI | Campbell Park, Milton Keynes | Results |
| 28 Jun 1999 | North Zone | Nottinghamshire Second XI v Yorkshire Second XI | Brian Wakefield Memorial Ground, Nottingham | Results |
| 28 Jun 1999 | South East Zone | Sussex Second XI v Marylebone Cricket Club Young Cricketers | Sea Lane, Middleton-on-Sea | Results |
| 28 Jun 1999 | South West Zone | Worcestershire Second XI v Glamorgan Second XI | Seth Somers Park, Halesowen | Results |
| 29 Jun 1999 | South West Zone | Glamorgan Second XI v Somerset Second XI | Sophia Gardens, Cardiff | Results |
| 29 Jun 1999 | Central Zone | Leicestershire Second XI v Middlesex Second XI | Coventry Road, Lutterworth | Results |
| 29 Jun 1999 | South East Zone | Marylebone Cricket Club Young Cricketers v Kent Second XI | Shenley Sports Ground, Shenley | Results |
| 29 Jun 1999 | North Zone | Nottinghamshire Second XI v Derbyshire Second XI | Station Lane, Farnsfield | Results |
| 29 Jun 1999 | North Zone | Yorkshire Second XI v Durham Second XI | Windy Hill Lane, Marske-by-the-Sea | Results |
| 30 Jun 1999 | South West Zone | Hampshire Second XI v Gloucestershire Second XI | County Ground, Southampton | Results |
| 30 Jun 1999 | South East Zone | Kent Second XI v Essex Second XI | Spitfire Ground, St Lawrence, Canterbury | Results |
| 30 Jun 1999 | North Zone | Lancashire Second XI v Derbyshire Second XI | Hare Hill, Littleborough | Results |
| 30 Jun 1999 | South East Zone | Sussex Second XI v Surrey Second XI | New County Ground, Hove | Results |
| 30 Jun 1999 | Central Zone | Warwickshire Second XI v Middlesex Second XI | Bulls Head Ground, Coventry | Results |
| 30 Jun 1999 | South West Zone | Worcestershire Second XI v Somerset Second XI | Main Road, Ombersley | Results |
| 01 Jul 1999 | North Zone | Durham Second XI v Derbyshire Second XI | Hornby Park, Seaton Carew | Results |
| 01 Jul 1999 | South West Zone | Glamorgan Second XI v Worcestershire Second XI | Spytty Park, Newport | Results |
| 01 Jul 1999 | Central Zone | Leicestershire Second XI v Warwickshire Second XI | Coventry Road, Lutterworth | Results |
| 01 Jul 1999 | North Zone | Yorkshire Second XI v Nottinghamshire Second XI | Wagon Lane, Bingley | Results |
| 02 Jul 1999 | North Zone | Derbyshire Second XI v Lancashire Second XI | Repton School Ground, Repton | Results |
| 02 Jul 1999 | North Zone | Durham Second XI v Nottinghamshire Second XI | Seat Unique Riverside Ground, Chester-le-Street | Results |
| 02 Jul 1999 | South East Zone | Kent Second XI v Surrey Second XI | Spitfire Ground, St Lawrence, Canterbury | Results |
| 02 Jul 1999 | South East Zone | Sussex Second XI v Essex Second XI | New County Ground, Hove | Results |
| 02 Jul 1999 | South West Zone | Worcestershire Second XI v Hampshire Second XI | Cherry Hill Road, Barnt Green | Results |
| 05 Jul 1999 | North Zone | Durham Second XI v Yorkshire Second XI | Sunderland Road, East Boldon | Results |
| 05 Jul 1999 | South West Zone | Gloucestershire Second XI v Somerset Second XI | Seat Unique Stadium, Bristol | Results |
| 05 Jul 1999 | South West Zone | Hampshire Second XI v Worcestershire Second XI | County Ground, Southampton | Results |
| 05 Jul 1999 | South East Zone | Kent Second XI v Sussex Second XI | Spitfire Ground, St Lawrence, Canterbury | Results |
| 05 Jul 1999 | North Zone | Lancashire Second XI v Nottinghamshire Second XI | Emirates Old Trafford, Manchester | Results |
| 05 Jul 1999 | Central Zone | Middlesex Second XI v Leicestershire Second XI | Corfton Road, Ealing | Results |
| 05 Jul 1999 | South East Zone | Surrey Second XI v Essex Second XI | The Kia Oval, Kennington | Results |
| 06 Jul 1999 | North Zone | Derbyshire Second XI v Nottinghamshire Second XI | Christchurch Meadows, Belper | Results |
| 06 Jul 1999 | South West Zone | Somerset Second XI v Worcestershire Second XI | The Cooper Associates County Ground, Taunton | Results |
| 06 Jul 1999 | South East Zone | Surrey Second XI v Kent Second XI | The Kia Oval, Kennington | Results |
| 06 Jul 1999 | Central Zone | Warwickshire Second XI v Leicestershire Second XI | Sandwell Park, West Bromwich | Results |
| 07 Jul 1999 | South West Zone | Glamorgan Second XI v Hampshire Second XI | Eugene Cross Park, Ebbw Vale | Results |
| 07 Jul 1999 | North Zone | Lancashire Second XI v Yorkshire Second XI | Emirates Old Trafford, Manchester | Results |
| 07 Jul 1999 | Central Zone | Middlesex Second XI v Warwickshire Second XI | Corfton Road, Ealing | Results |
| 07 Jul 1999 | North Zone | Nottinghamshire Second XI v Durham Second XI | Oakfeld Lane, Warsop | Results |
| 07 Jul 1999 | South East Zone | Sussex Second XI v Kent Second XI | Recreation Ground, Haywards Heath | Results |
| 08 Jul 1999 | North Zone | Derbyshire Second XI v Durham Second XI | North Road, Glossop | Results |
| 08 Jul 1999 | Central Zone | Northamptonshire Second XI v Minor Counties Under-25s | Orlingbury Road, Isham | Results |
| 08 Jul 1999 | North Zone | Nottinghamshire Second XI v Lancashire Second XI | Worksop College Ground, Worksop | Results |
| 08 Jul 1999 | South West Zone | Somerset Second XI v Glamorgan Second XI | The Cooper Associates County Ground, Taunton | Results |
| 08 Jul 1999 | South East Zone | Surrey Second XI v Marylebone Cricket Club Young Cricketers | The Kia Oval, Kennington | Results |
| 09 Jul 1999 | South East Zone | Essex Second XI v Sussex Second XI | The Toby Howe Cricket Ground, Billericay | Results |
| 09 Jul 1999 | South East Zone | Kent Second XI v Marylebone Cricket Club Young Cricketers | Mote Park, Maidstone | Results |
| 09 Jul 1999 | Central Zone | Minor Counties Under-25s v Leicestershire Second XI | The Green, North Runcton | Results |
| 09 Jul 1999 | South West Zone | Somerset Second XI v Hampshire Second XI | The Cooper Associates County Ground, Taunton | Results |
| 09 Jul 1999 | Central Zone | Warwickshire Second XI v Northamptonshire Second XI | Arlington Avenue, Leamington Spa | Results |
| 12 Jul 1999 | South East Zone | Essex Second XI v Kent Second XI | Hare Field, Coggeshall | Results |
| 12 Jul 1999 | Central Zone | Northamptonshire Second XI v Warwickshire Second XI | County Ground, Northampton | Results |
| 13 Jul 1999 | Central Zone | Leicestershire Second XI v Northamptonshire Second XI | Uptonsteel County Ground, Leicester | Results |
| 15 Jul 1999 | North Zone | Durham Second XI v Lancashire Second XI | Ashbrooke, Sunderland | Results |
| 15 Jul 1999 | Central Zone | Leicestershire Second XI v Minor Counties Under-25s | Uptonsteel County Ground, Leicester | Results |
| 19 Jul 1999 | South East Zone | Surrey Second XI v Sussex Second XI | The Kia Oval, Kennington | Results |
| 26 Jul 1999 | Central Zone | Northamptonshire Second XI v Middlesex Second XI | Wellingborough School Ground, Wellingborough | Results |
| 16 Aug 1999 | Semi-Final | Hampshire Second XI v Durham Second XI | County Ground, Southampton | Results |
| 17 Aug 1999 | Semi-Final | Kent Second XI v Warwickshire Second XI | Spitfire Ground, St Lawrence, Canterbury | Results |
| 06 Sep 1999 | Final | Kent Second XI v Hampshire Second XI | Spitfire Ground, St Lawrence, Canterbury | Results |
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