| 18 May 1986 | First Round | Hungerford v Penton | War Memorial Ground, Hungerford | Results |
| 18 May 1986 | First Round | Basics v ITW Basingstoke | Down Grange Playing Fields, Basingstoke | Results |
| 18 May 1986 | First Round | Steeple Langford v Hale | Langford Recreation Ground, Steeple Langford | Results |
| 18 May 1986 | First Round | Michelmersh and Timsbury v Olivers Battery | Mannyngham Way, Timsbury | Results |
| 01 Jun 1986 | Second Round | not known v Longparish | not known | Results |
| 01 Jun 1986 | Second Round | Andover v Wherwell | Batchelors Barn Road, Andover | Results |
| 01 Jun 1986 | Second Round | not known v Old Basing | not known | Results |
| 01 Jun 1986 | Second Round | Hook and Newnham v Tilehurst | King George V Playing Field, Hook | Results |
| 01 Jun 1986 | Second Round | not known v Hyde | not known | Results |
| 01 Jun 1986 | Second Round | Ellingham v Bashley (Rydal) | Pickett Post, Ringwood | Results |
| 01 Jun 1986 | Second Round | Worthies Sports v Polhill | Recreation Ground, Kings Worthy | Results |
| 01 Jun 1986 | Second Round | not known v Castle | not known | Results |
| 01 Jun 1986 | Second Round | Alverstoke v Crofton | Gosport Park, Gosport | Results |
| 01 Jun 1986 | Second Round | Purbrook and Portsdown v Portsmouth Enterprise | Purbrook Heath, Purbrook | Results |
| 01 Jun 1986 | Second Round | Hambledon v Rowledge | Ridge Meadow, Hambledon | Results |
| 01 Jun 1986 | Second Round | Denmead v Waterlooville | King George V Playing Field, Denmead | Results |
| 01 Jun 1986 | Second Round | Sarisbury Athletic v West End | The Hollow, Sarisbury | Results |
| 01 Jun 1986 | Second Round | Maybush Community v St Cross | Millbrook Secondary School, Millbrook | Results |
| 01 Jun 1986 | Second Round | Road Sea v BAT Sports | Road Sea Park, Marchwood | Results |
| 15 Jun 1986 | Third Round | not known v Longparish | not known | Results |
| 15 Jun 1986 | Third Round | not known v Old Basing | not known | Results |
| 15 Jun 1986 | Third Round | not known v Bashley (Rydal) | not known | Results |
| 15 Jun 1986 | Third Round | Worthies Sports v not known | Recreation Ground, Kings Worthy | Results |
| 15 Jun 1986 | Third Round | not known v Crofton | not known | Results |
| 15 Jun 1986 | Third Round | Hambledon v not known | Ridge Meadow, Hambledon | Results |
| 15 Jun 1986 | Third Round | Sarisbury Athletic v not known | The Hollow, Sarisbury | Results |
| 15 Jun 1986 | Third Round | not known v BAT Sports | not known | Results |
| 29 Jun 1986 | Quarter Final | Bashley (Rydal) v Worthies Sports | Bashley Road, Bashley | Results |
| 29 Jun 1986 | Quarter Final | Old Basing v Longparish | Old Basing Recreation Ground, Old Basing | Results |
| 29 Jun 1986 | Quarter Final | Hambledon v Crofton | Ridge Meadow, Hambledon | Results |
| 29 Jun 1986 | Quarter Final | BAT Sports v Sarisbury Athletic | Southern Gardens, Totton | Results |
| 13 Jul 1986 | Semi Final | Bashley (Rydal) v Old Basing | Hampshire County Council Sports Ground, Winchester | Results |
| 13 Jul 1986 | Semi Final | BAT Sports v Crofton | Southern Gardens, Totton | Results |
| 27 Jul 1986 | Final | Bashley (Rydal) v Crofton | The Quarters, Hursley | Results |
| 22 May 1986 | First Round | Esso Fawley v Calmore Sports | Fawley Cricket Club Ground, Holbury | Results |
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