| 30 Apr 1986 | First Round | Banchory v Rossie Priory | Burnett Park, Banchory | Results |
| 04 May 1986 | First Round | Madras College Former Pupils v Stoneywood | Station Park, St Andrews | Results |
| 11 May 1986 | First Round | Cults v Luncarty | Allan Park, Cults | Results |
| 30 Apr 1986 | First Round | University of St Andrews v Ellon Gordon | University Park, St Andrews | Results |
| 30 Apr 1986 | First Round | Dyce v Crosshill | not known | Results |
| 04 May 1986 | First Round | Leven v Inverurie | King George V Park, Leven | Results |
| 30 Apr 1986 | First Round | Banff v Kinloch | Banff Cricket Club Ground, Banff | Results |
| 11 May 1986 | First Round | Lawside v Dundee University Staff | Lochee Park, Dundee | Results |
| 30 Apr 1986 | First Round | Breadalbane v Kingsway | Victoria Park, Aberfeldy | Results |
| 11 May 1986 | First Round | Royal Air Force Leuchars v Crieff | Royal Air Force Ground, Leuchars | Results |
| 27 Apr 1986 | First Round | Broomhall v Glendelvine | The Cairns, Charlestown | Results |
| 30 Apr 1986 | First Round | Perth Northern v Largo | Doo'cot Park No 1, Perth | Results |
| 30 Apr 1986 | First Round | Norwood v Waid | Lochee Park, Dundee | Results |
| 11 May 1986 | First Round | Livingston and District v HMS Gannet | Bangour Village Hospital, Dechmont | Results |
| 30 Apr 1986 | First Round | Stranraer v Eaglesham | Stranraer Cricket Club Ground, Stranraer | Results |
| 30 Apr 1986 | First Round | Marchmont v Strathclyde | Cavalry Park, Edinburgh | Results |
| 11 May 1986 | First Round | Westquarter and Redding v Tynecastle | Blairlodge, Brightons | Results |
| 30 Apr 1986 | First Round | St Michael's v Redbrae | Kingholm Park, Dumfries | Results |
| 30 Apr 1986 | First Round | Glenkens v Ardeer | Glenkens Cricket Club Ground, Glenkens | Results |
| 30 Apr 1986 | First Round | DAFS v London Road | not known | Results |
| 11 May 1986 | First Round | St Modan's High School Former Pupils v Trinity Academicals | Bluebellwood Park, Bannockburn | Results |
| 30 Apr 1986 | First Round | Edinburgh University Staff v Bishopbriggs | Peffermill Playing Fields, Edinburgh | Results |
| 20 Apr 1986 | First Round | Queen's Park (Scotland) v Drummond | Queen's Park, Glasgow | Results |
| 04 May 1986 | First Round | Thornliebank v Peebles County | Muirend, Thornliebank | Results |
| 04 May 1986 | First Round | Scotts v Garrowhill | Battery Park, Greenock | Results |
| 04 May 1986 | First Round | Weirs v Mitre | Albert Park, Glasgow | Results |
| 30 Apr 1986 | First Round | Royal Botanic Gardens v Boroughmuir | not known | Results |
| 11 May 1986 | First Round | Gargunnock Village v Rolls Royce | Williamfield, Stirling | Results |
| 27 Apr 1986 | First Round | Jerviswood v Britoil | Allanton Playing Fields, Ralston | Results |
| 30 Apr 1986 | First Round | Honeywell v Life Assurance of Scotland | not known | Results |
| 30 Apr 1986 | First Round | Musselburgh v City of Edinburgh Pakistan Association | Lewisvale Park, Musselburgh | Results |
| 30 Apr 1986 | First Round | Cumbernauld v Alva | Cumbernauld Cricket Club Ground, Cumbernauld | Results |
| 25 May 1986 | Second Round | Crieff v not known | not known | Results |
| 25 May 1986 | Second Round | Dyce v not known | not known | Results |
| 25 May 1986 | Second Round | Ellon Gordon v not known | not known | Results |
| 25 May 1986 | Second Round | Marchmont v not known | not known | Results |
| 25 May 1986 | Second Round | not known v not known | not known | Results |
| 25 May 1986 | Second Round | not known v not known | not known | Results |
| 25 May 1986 | Second Round | not known v not known | not known | Results |
| 25 May 1986 | Second Round | not known v not known | not known | Results |
| 25 May 1986 | Second Round | not known v not known | not known | Results |
| 25 May 1986 | Second Round | not known v not known | not known | Results |
| 25 May 1986 | Second Round | not known v not known | not known | Results |
| 25 May 1986 | Second Round | not known v not known | not known | Results |
| 25 May 1986 | Second Round | not known v not known | not known | Results |
| 25 May 1986 | Second Round | not known v not known | not known | Results |
| 25 May 1986 | Second Round | not known v not known | not known | Results |
| 25 May 1986 | Second Round | not known v not known | not known | Results |
| 15 Jun 1986 | Third Round | Crieff v not known | not known | Results |
| 15 Jun 1986 | Third Round | Dyce v not known | not known | Results |
| 15 Jun 1986 | Third Round | Ellon Gordon v not known | not known | Results |
| 15 Jun 1986 | Third Round | Marchmont v not known | not known | Results |
| 15 Jun 1986 | Third Round | not known v not known | not known | Results |
| 15 Jun 1986 | Third Round | not known v not known | not known | Results |
| 15 Jun 1986 | Third Round | not known v not known | not known | Results |
| 15 Jun 1986 | Third Round | not known v not known | not known | Results |
| 06 Jul 1986 | Quarter-Final | Crieff v not known | not known | Results |
| 06 Jul 1986 | Quarter-Final | Dyce v not known | not known | Results |
| 06 Jul 1986 | Quarter-Final | Ellon Gordon v not known | not known | Results |
| 06 Jul 1986 | Quarter-Final | Marchmont v not known | not known | Results |
| 27 Jul 1986 | Semi-Final | Crieff v not known | not known | Results |
| 27 Jul 1986 | Semi-Final | Dyce v not known | not known | Results |
| 10 Aug 1986 | Final | Ellon Gordon v Marchmont | Duffus Park, Cupar | Results |
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