| 03 Sep 1999 | Final | Teddington v Wolverhampton | Lord's Cricket Ground, St John's Wood | Results |
| 02 May 1999 | Group 2 (North East I) Second Round | Percy Main v Morpeth | St John's Green, Percy Main | Results |
| 09 May 1999 | Group 2 (North East I) Second Round | Benwell Hill v Benwell and Walbottle | Denton Bank, Benwell Hill | Results |
| 16 May 1999 | Group 2 (North East I) Second Round | Backworth v Sunderland | Backworth Percy Welfare Centre, Backworth | Results |
| 16 May 1999 | Group 2 (North East I) Second Round | Gateshead Fell v Ashington | Eastwood Gardens, Gateshead | Results |
| 17 May 1999 | Group 2 (North East I) Third Round | Tynemouth v Stockton | Preston Avenue, North Shields | Results |
| 23 May 1999 | Group 2 (North East I) Third Round | Percy Main v Tynedale | St John's Green, Percy Main | Results |
| 24 May 1999 | Group 2 (North East I) Second Round | Lintz v South Northumberland | Lumley Gardens, Lintz | Results |
| 30 May 1999 | Group 2 (North East I) Third Round | Backworth v Benwell Hill | Backworth Percy Welfare Centre, Backworth | Results |
| 01 Jun 1999 | Group 2 (North East I) Third Round | Gateshead Fell v South Northumberland | Eastwood Gardens, Gateshead | Results |
| 15 Jun 1999 | Group 2 (North East I) Fourth Round | South Northumberland v Percy Main | Roseworth Terrace, Gosforth | Results |
| 21 Jun 1999 | Group 2 (North East I) Fourth Round | Tynemouth v Benwell Hill | Preston Avenue, North Shields | Results |
| 04 Jul 1999 | Group 2 (North East I) Fifth Round | South Northumberland v Benwell Hill | Roseworth Terrace, Gosforth | Results |
| 11 Jul 1999 | Group 2 (North East I) Sixth Round | South Northumberland v Clydesdale | Roseworth Terrace, Gosforth | Results |
| 07 May 1999 | Third Round | Chingford v Wimbledon | Forest Side, Chingford | Results |
| 02 May 1999 | First Round | Chingford v Sunbury | Forest Side, Chingford | Results |
| 09 May 1999 | Second Round | Cheam v Chingford | Peaches Close, Cheam | Results |
| 13 Jun 1999 | Fourth Round | Chingford v Bromley | Forest Side, Chingford | Results |
| 09 May 1999 | | Purley v Saffron Walden | The Ridge, Purley | Results |
| 23 May 1999 | | Saffron Walden v Sevenoaks Vine | Anglo-American Playing Fields, Saffron Walden | Results |
| 03 May 1999 | First Round | Treeton Welfare v Cleethorpes | Washfield Lane, Treeton | Results |
| 25 Apr 1999 | First Round | Finchampstead v High Wycombe | Finchampstead Park, Finchampstead | Results |
| 09 May 1999 | Second Round | Farnham v Finchampstead | Folly Hill, Farnham | Results |
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