| First Round |
| 22/09/98 | AFC Totton | 7 | Romsey Town | 1 |
| 09/12/98 | Alton Town | 5 | Hamble ASSC | 1 |
| 03/10/98 | B.A.T. Sports | 2 | Moneyfields After Extra Time. Moneyfields won 4-2 on penalties |
2 |
| 07/10/98 | Bemerton Heath Harlequins | 2 | Colden Common | 0 |
| 06/10/98 | Brockenhurst | 1 | Eastleigh | 2 |
| 22/09/98 | Christchurch | 4 | Horndean | 0 |
| 27/10/98 | Cove | 2 | Blackfield & Langley | 7 |
| 21/10/98 | Downton | 3 | Petersfield Town | 1 |
| 30/09/98 | Fareham Town | 3 | Winchester City | 0 |
| 20/10/98 | Gosport Borough | 0 | Fleetlands | 1 |
| 24/10/98 | Pirelli General | 0 | Queens Keep | 1 |
| 14/11/98 | RS Basingstoke A. E. T. RS Basingstoke won 4-3 on pens. |
2 | Mayflower West Wight | 2 |
| 20/10/98 | Whitchurch United | 3 | Winchester Castle After Extra Time. Winchester Castle won 4-3 on penalties |
3 |
Exemptions to Round 2 : Fleet Town, Havant & Waterlooville, Lymington & New Milton
| Second Round |
| 26/01/99 | AFC Totton | 2 | Fareham Town | 1 |
| 02/02/99 | Alton Town | 2 | Fleet Town | 3 |
| 24/02/99 | Blackfield & Langley | 1 | Christchurch | 2 |
| 03/03/99 | Downton | 0 | Moneyfields | 2 |
| 10/02/99 | Eastleigh | 3 | Bemerton Heath Harlequins | 1 |
| 15/12/98 | Havant &
Waterlooville Withdrew from competition |
w/o | Fleetlands Walkover for Fleetlands |
w/o |
| 13/03/99 | Lymington & New Milton | 8 | Winchester Castle | 0 |
| 30/01/99 | RS Basingstoke | 4 | Queens Keep | 2 |
| Quarter Finals |
| 09/03/99 | Christchurch | 0 | AFC Totton | 2 |
| 17/03/99 | Eastleigh | 4 | RS Basingstoke | 1 |
| 18/03/99 | Lymington & New Milton | 4 | Fleetlands | 0 |
| 22/04/99 | Moneyfields | 3 | Fleet Town | 0 |
| Semi Finals |
| 13/04/99 | AFC Totton | 2 | Eastleigh | 1 |
| 05/05/99 | Lymington & New Milton | 0 | Moneyfields After Extra Time. Moneyfields won 4-2 on penalties |
0 |
| FINAL |
| 11/05/99 | AFC Totton | 1 | Moneyfields | 0 |
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