| 04 Jul 1999 | Quarter-Final | Kent Nomads Women v Wakefield Women | Wellingborough School Ground, Wellingborough | Results |
| 04 Jul 1999 | Quarter-Final | Derby Women v Kent Invicta Women | Finchampstead Park, Finchampstead | Results |
| 04 Jul 1999 | Quarter-Final | Redoubtables Women v Thrumpton Women | Arlington Avenue, Leamington Spa | Results |
| 04 Jul 1999 | Quarter-Final | North Riding Women v Wallington Women | Graham Solley Sports Development Centre, Sheffield | Results |
| 14 Aug 1999 | Semi-Final | Kent Invicta Women v North Riding Women | Worksop College Ground, Worksop | Results |
| 14 Aug 1999 | Semi-Final | Thrumpton Women v Wakefield Women | Wrekin College Ground, Wellington | Results |
| 12 Sep 1999 | Final | North Riding Women v Thrumpton Women | Brunton Memorial Ground, Radlett | Results |
| 02 May 1999 | First Round | Riverside Women v Shepperton Women | Fuller, Smith and Turner Ground, Chiswick | Results |
| 25 Apr 1999 | Preliminary Round | Holmesdale Women v Kent Nomads Women | not known | Results |
| 25 Apr 1999 | Preliminary Round | Wootton Bassett Ladies v St Fagans Women | not known | Results |
| 25 Apr 1999 | Preliminary Round | Taunton Women v Hambledon Women | not known | Results |
| 25 Apr 1999 | Preliminary Round | Redoubtables Women Second XI v Brighton and Hove Women | not known | Results |
| 25 Apr 1999 | Preliminary Round | Riverside Women v Honor Oak Women | not known | Results |
| 25 Apr 1999 | Preliminary Round | Englefield Green Women v Dukesmead Women | not known | Results |
| 25 Apr 1999 | Preliminary Round | Shepperton Women Second XI v Addiscombe Women | not known | Results |
| 25 Apr 1999 | Preliminary Round | Hitchin Women v Radlett Vagabonds Women | not known | Results |
| 25 Apr 1999 | Preliminary Round | Salford Women v Fulwood and Broughton Women | not known | Results |
| 25 Apr 1999 | Preliminary Round | Anston Women v Sheffield United Ladies | not known | Results |
| 25 Apr 1999 | Preliminary Round | Leicester Women v Hatfield Town Women | not known | Results |
| 25 Apr 1999 | Preliminary Round | Stocksfield Women v Shotley Bridge Women | not known | Results |
| 02 May 1999 | First Round | Kent Nomads Women v Old Stacians Women | not known | Results |
| 02 May 1999 | First Round | Somerset Wanderers Women v Wootton Bassett Ladies | not known | Results |
| 02 May 1999 | First Round | Ridgeway Women v Hambledon Women | not known | Results |
| 02 May 1999 | First Round | Brighton and Hove Women v Wallington Women | not known | Results |
| 02 May 1999 | First Round | Redoubtables Women v Dukesmead Women | not known | Results |
| 02 May 1999 | First Round | Kent Invicta Women v Shepperton Women Second XI | not known | Results |
| 02 May 1999 | First Round | Radlett Vagabonds Women v Gunnersbury Women | not known | Results |
| 02 May 1999 | First Round | Salford Women v Wakefield Women | not known | Results |
| 02 May 1999 | First Round | Wolverhampton Ladies v Evesham Women | not known | Results |
| 02 May 1999 | First Round | Sheffield United Ladies v Thrumpton Women | not known | Results |
| 02 May 1999 | First Round | Hatfield Town Women v Cambridge Women | not known | Results |
| 02 May 1999 | First Round | Derby Women v Laytons Women | not known | Results |
| 02 May 1999 | First Round | North Riding Women v Shotley Bridge Women | not known | Results |
| 02 May 1999 | First Round | Littleborough Women v City of Leeds Women | not known | Results |
| 23 May 1999 | Second Round | Kent Nomads Women v Somerset Wanderers Women | not known | Results |
| 23 May 1999 | Second Round | Ridgeway Women v Wallington Women | not known | Results |
| 23 May 1999 | Second Round | Shepperton Women v Redoubtables Women | not known | Results |
| 23 May 1999 | Second Round | Kent Invicta Women v Gunnersbury Women | not known | Results |
| 23 May 1999 | Second Round | Wolverhampton Ladies v Thrumpton Women | not known | Results |
| 23 May 1999 | Second Round | Hatfield Town Women v Derby Women | not known | Results |
| 23 May 1999 | Second Round | North Riding Women v City of Leeds Women | not known | Results |
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