| 04 May 1999 | 1st Round | Netherlands v Cambridgeshire | Sportpark Het Schootsveld, Deventer | Results |
| 04 May 1999 | 1st Round | Bedfordshire v Huntingdonshire | Wardown Park, Luton | Results |
| 04 May 1999 | 1st Round | Berkshire v Warwickshire Cricket Board | Sonning Lane, Reading | Results |
| 04 May 1999 | 1st Round | Cumberland v Cornwall | Parkside Road, Kendal | Results |
| 04 May 1999 | 1st Round | Durham Cricket Board v Oxfordshire | Park Drive, Hartlepool | Results |
| 04 May 1999 | 1st Round | Gloucestershire Cricket Board v Yorkshire Cricket Board | North Park, Cheltenham | Results |
| 04 May 1999 | 1st Round | Hertfordshire v Leicestershire Cricket Board | Brunton Memorial Ground, Radlett | Results |
| 04 May 1999 | 1st Round | Kent Cricket Board v Denmark | Mote Park, Maidstone | Results |
| 04 May 1999 | 1st Round | Lincolnshire v Wales Minor Counties | London Road, Sleaford | Results |
| 04 May 1999 | 1st Round | Northamptonshire Cricket Board v Wiltshire | County Ground, Northampton | Results |
| 04 May 1999 | 1st Round | Northumberland v Ireland | Osborne Avenue, Jesmond | Results |
| 04 May 1999 | 1st Round | Scotland v Nottinghamshire Cricket Board | Boghall, Linlithgow | Results |
| 04 May 1999 | 1st Round | Suffolk v Hampshire Cricket Board | The Victory Ground, Bury St Edmunds | Results |
| 04 May 1999 | 1st Round | Surrey Cricket Board v Norfolk | Peaches Close, Cheam | Results |
| 17 May 1999 | 2nd Round | Somerset Cricket Board v Bedfordshire | The Cooper Associates County Ground, Taunton | Results |
| 19 May 1999 | 2nd Round | Derbyshire Cricket Board v Wales Minor Counties | Deer Park, Dunstall | Results |
| 19 May 1999 | 2nd Round | Devon v Berkshire | The Recreation Ground, Torquay | Results |
| 19 May 1999 | 2nd Round | Durham Cricket Board v Staffordshire | Eastwood Gardens, Gateshead | Results |
| 19 May 1999 | 2nd Round | Herefordshire v Wiltshire | The Parks, Brockhampton | Results |
| 19 May 1999 | 2nd Round | Hertfordshire v Sussex Cricket Board | Balls Park, Hertford | Results |
| 19 May 1999 | 2nd Round | Ireland v Essex Cricket Board | Ormeau, Belfast | Results |
| 19 May 1999 | 2nd Round | Kent Cricket Board v Worcestershire Cricket Board | Mote Park, Maidstone | Results |
| 19 May 1999 | 2nd Round | Lancashire Cricket Board v Netherlands | Aigburth, Liverpool | Results |
| 19 May 1999 | 2nd Round | Middlesex Cricket Board v Cumberland | John Walker's Ground, Southgate | Results |
| 19 May 1999 | 2nd Round | Scotland v Dorset | Hamilton Crescent, Glasgow | Results |
| 19 May 1999 | 2nd Round | Shropshire v Hampshire Cricket Board | Orleton Park, Wellington | Results |
| 19 May 1999 | 2nd Round | Surrey Cricket Board v Cheshire | Church Road, Wimbledon | Results |
| 19 May 1999 | 2nd Round | Yorkshire Cricket Board v Buckinghamshire | Abbeydale Park, Sheffield | Results |
| 23 Jun 1999 | 3rd Round | Netherlands v Durham | VRA Ground, Amstelveen | Results |
| 23 Jun 1999 | 3rd Round | Bedfordshire v Derbyshire | Wardown Park, Luton | Results |
| 23 Jun 1999 | 3rd Round | Buckinghamshire v Warwickshire | Pound Lane, Marlow | Results |
| 23 Jun 1999 | 3rd Round | Cheshire v Kent | South Downs Road, Bowdon | Results |
| 23 Jun 1999 | 3rd Round | Cumberland v Sussex | Parkside Road, Kendal | Results |
| 23 Jun 1999 | 3rd Round | Devon v Worcestershire | The Maer Ground, Exmouth | Results |
| 23 Jun 1999 | 3rd Round | Durham Cricket Board v Gloucestershire | Seat Unique Riverside Ground, Chester-le-Street | Results |
| 23 Jun 1999 | 3rd Round | Hampshire Cricket Board v Glamorgan | County Ground, Southampton | Results |
| 23 Jun 1999 | 3rd Round | Herefordshire v Yorkshire | The Recreation Ground, Kington | Results |
| 23 Jun 1999 | 3rd Round | Hertfordshire v Lancashire | Brunton Memorial Ground, Radlett | Results |
| 23 Jun 1999 | 3rd Round | Ireland v Leicestershire | Castle Avenue, Dublin | Results |
| 23 Jun 1999 | 3rd Round | Kent Cricket Board v Hampshire | Spitfire Ground, St Lawrence, Canterbury | Results |
| 23 Jun 1999 | 3rd Round | Northamptonshire v Essex | County Ground, Northampton | Results |
| 23 Jun 1999 | 3rd Round | Nottinghamshire v Middlesex | Trent Bridge, Nottingham | Results |
| 23 Jun 1999 | 3rd Round | Scotland v Surrey | Raeburn Place, Edinburgh | Results |
| 23 Jun 1999 | 3rd Round | Wales Minor Counties v Somerset | St Helen's, Swansea | Results |
| 07 Jul 1999 | 4th Round | Netherlands v Kent | VRA Ground, Amstelveen | Results |
| 07 Jul 1999 | 4th Round | Glamorgan v Warwickshire | Sophia Gardens, Cardiff | Results |
| 07 Jul 1999 | 4th Round | Gloucestershire v Derbyshire | Seat Unique Stadium, Bristol | Results |
| 07 Jul 1999 | 4th Round | Hampshire v Lancashire | County Ground, Southampton | Results |
| 07 Jul 1999 | 4th Round | Northamptonshire v Nottinghamshire | County Ground, Northampton | Results |
| 07 Jul 1999 | 4th Round | Sussex v Somerset | New County Ground, Hove | Results |
| 07 Jul 1999 | 4th Round | Worcestershire v Surrey | Visit Worcestershire New Road, Worcester | Results |
| 07 Jul 1999 | 4th Round | Yorkshire v Leicestershire | Headingley, Leeds | Results |
| 28 Jul 1999 | Quarter-Final | Glamorgan v Gloucestershire | Sophia Gardens, Cardiff | Results |
| 28 Jul 1999 | Quarter-Final | Lancashire v Yorkshire | Emirates Old Trafford, Manchester | Results |
| 28 Jul 1999 | Quarter-Final | Northamptonshire v Surrey | County Ground, Northampton | Results |
| 28 Jul 1999 | Quarter-Final | Somerset v Kent | The Cooper Associates County Ground, Taunton | Results |
| 14 Aug 1999 | Semi-Final | Somerset v Surrey | The Cooper Associates County Ground, Taunton | Results |
| 15 Aug 1999 | Semi-Final | Gloucestershire v Yorkshire | Seat Unique Stadium, Bristol | Results |
| 29 Aug 1999 | Final | Gloucestershire v Somerset | Lord's Cricket Ground, St John's Wood | Results |
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