| WEDNESDAY 19th AUGUST 2009 | |||
| EAST REGION - DJ Laing North League Cup - Section 2 | Referee | ||
| Kirriemuir Thistle | 1-5 | Blairgowrie | Colin Duncan |
| Forfar Albion | 0-5 | Forfar West End | Jeff Banks |
| EAST REGION - DJ Laing North League Cup - Section 3 | |||
| Dundee Violet | 3-7 | Tayport | Gavin Harris |
| Lochee Harp | 1-6 | Lochee United | Kersten Schroeder |
| EAST REGION - ACA Sports Central League Cup - Section 1 | Referee | ||
| Hill of Beath Hawthorn | 6-2 | Oakley United | Raymond Whyte |
| Crossgates Primrose | 2-4 | Steelend Victoria | Michael Gill |
| EAST REGION - ACA Sports Central League Cup - Section 2 | |||
| Jeanfield Swifts | 3-1 | Kinnoull | Ross McIntyre |
| Luncarty | 2-3 | Bankfoot Athletic | Stuart Stevenson |
| EAST REGION - ACA Sports Central League Cup - Section 3 | |||
| Glenrothes | 3-2 | Kirkcaldy YMCA | Allan Spalding |
| Newburgh | 1-6 | St. Andrews United | Lorraine Clark |
| EAST REGION - ACA Sports Central League Cup - Section 4 | |||
| Dundonald Bluebell | 1-2 | Lochgelly Albert | Paul Simmons |
| Ballingry Rovers | 5-3 | Kelty Hearts | Dougie Potter |
| EAST REGION - Dechmont South League Cup - Section 1 | Referee | ||
| Edinburgh United | 2-0 | Dalkeith Thistle | Gianluca Marini |
| EAST REGION - Dechmont South League Cup - Section 2 | |||
| Harthill Royal | 1-0 | Sauchie | Graeme Leslie |
| Blackburn United | 0-5 | Bathgate Thistle | Gavin Duncan |
| Stoneyburn | 2-2 | Livingston United | Scott Jamieson |
| EAST REGION - Dechmont South League Cup - Section 3 | |||
| Pumpherston | 1-4 | Armadale Thistle | Declan Reid |
| Newtongrange Star | 2-3 | Linlithgow Rose | Neil McLennan |
| West Calder United | 2-6 | Spartans | Ralph Gordon |
| EAST REGION - Dechmont South League Cup - Section 4 | |||
| Musselburgh Athletic | 4-0 | Haddington Athletic | Paul Reid |
| Dunbar United | 0-4 | Arniston Rangers | William MacKenzie |