The 2009 MacAulay Cup draw was made live on Oban fm on Saturday 6 December 2008.
The tie of the first round is Newtonmore's home clash with Fort William. The winners take on the side which comes out on top between newly appointed managers Ali Ferguson of Lochaber and Garry Reid of Strathglass.
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| MacAulay Cup Draw |
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| (North) 1st Round |
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| Glenurquhart |
v |
Lovat |
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| Lochaber |
v |
Strathglass |
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| Newtonmore |
v |
Fort William |
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| Kingussie |
v |
Kilmallie |
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| (North) Quarter Final |
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| Newtonmore / Fort William |
v |
Lochaber / Strathglass |
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| Kingussie / Kilmallie |
v |
Glenurquhart / Lovat |
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| (South) 1st Round |
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| Oban Camanachd |
v |
Glasgow Mid Argyll |
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| Glenorchy |
v |
Kilmory |
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| Inveraray |
v |
Kyles Athletic |
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| Ballachulish / Tayforth |
v |
Bute |
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| (South) Quarter Final |
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| Inveraray / Kyles Athletic |
v |
Ballachulish / Tayforth / Bute |
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| Glenorchy / Kilmory |
v |
Oban Camanachd / Glasgow Mid Argyll |
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