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| Title holder Steven McEwan |
Joining holder Steven McEwan (Loudoun) in the draw for the fist and second round matches were the Club Champions or runners up from the majority of clubs in the county.
McEwan begins the defence of his title, and his bid for a third successive win in the competition, with a tough away tie against Robbie Fulker at Kilmarnock Barassie.
The full draw for the first and second round matches is :-
| 1st Round | 2nd Round |
| Played By:- 13th April 2014 | Played By:- 18th May 2014 |
| SCOTT MCCUNE (Moorpark) | |
| KEVIN COUPLAND (Malletsheugh) | |
| MALCOLM PENNYCOTT (Whiting Bay) | |
| IAN McKENZIE (Saxone) | |
| KENNY MILLIKEN (Troon St Meddans) | |
| DAVID TAYLOR (AyrSeafield) | |
| GORDON BOYLE (Turnberry) | |
| BILLY SMITH (Caprington) | |
| DAVID MASON (Ayr Dalmilling) | |
| KENNY MACASKILL (Turnberry Staff) | |
| GRAHAM McLAUGHLAN (Troon Portland) | |
| GARY STEELE (Maybole) | |
| SANDY RIDDELL (Skelmorlie) | |
| GARY JORDAN (Crosshouse) | |
| DAVID COOK (Fenwick) | |
| CRAIG ROBERTSON (Abbotsford) | |
| STUART ROBIN (Prestwick St Nicholas) | |
| ADAM SWEENEY (Largs Routenburn) | |
| COLIN BERRY (Rowallan Castle) | |
| JAMES GRAHAM (Doon Valley) | |
| GRAEME GIMSON (Prestwick St Cuthbert) | |
| DARREN MALLINSON (Irvine Ravenspark) | |
| CRAIG ANDERSON (Ayr Carrick) | |
| IAIN MACDONALD (Largs) | |
| CRAIG HAMILTON (Ballochmyle) | |
| IAN HARDING (North Beach) | |
| ROBBIE E. FULKER (Kilmarnock Barassie) | |
| STEVEN McEWAN (Holder) | |
| ANDREW JESS (Ayr Belleisle) | |
| STEVEN BOLLAND (Tam 'O' Shanter) | |
| THOMAS FREER Jr (Alton) | |
| CRAIG YOUNG (Loudoun) | |
| FRANK MURDOCH (Brunston Castle) | |
| ROBIN McCAIG (West Kilbride) | |
| STEPHEN BROWN (Drongan) | |
| COLIN CRAIG (Troon Welbeck) | |
| JAMES PATTERSON (Braehead) | |
| DEREK BALLANTYNE (Ardeer) | |
| BRYAN JAMIESON (Wallacetown) | |
| JOHN SHANKS (Irvine) | |
| ANDREW ARMSTRONG (Auchenharvie 88) | |
| GORDON C. McKELVIE (Royal Troon) | |
| TOM REID (Stewarton) | |
| ALAN SMEETON (The Chase) | |
| GARY BRYDEN (Girvan) | |
| MARTIN RIDDALL (New Cumnock) | |
| EWAN McKINNON (Brodick) | |
| IAIN GIRVAN (Muirkirk) | |
| ALAN McLEAN (Kilbirnie Place) | |
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