| 2009 Ontario Soccer League Annual Awards |
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| OSL Provincial East |
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| Leading Goal Scorer |
Mahyar Kohbad |
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Goldline |
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| Goalkeeper of the Year |
Tommaso Bianchi |
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G.S. United |
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Marko Paunkoski |
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| MVP of the Year |
Sergio Marchant |
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G.S. United |
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| Rookie of the Year |
Jordan Webb |
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G.S United |
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| OSL Provincial West |
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| Leading Goal Scorer |
Jason Shannon |
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Croatia Hamilton |
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| Goalkeeper of the Year |
Andrew Pierpoint |
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Caledon Celtic |
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Matthew Grant |
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| MVP of the Year |
Jamie Dodds |
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Croatia Hamilton |
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| Rookie of the Year |
Dani Jankovic |
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Croatia Hamilton |
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| OSL Central Region East |
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| Leading Goal Scorer |
Aidan O'Keeffe |
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Toronto Celtic |
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Chris Ciavarella |
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Hellenics |
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| Goalkeeper of the Year |
Fabrice Kabongo |
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Toronto Celtic |
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| MVP of the Year |
Mike Hadden |
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Toronto Celtic |
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| Rookie of the Year |
Jason Walker |
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Toronto Celtic |
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| OSL Central Region Central |
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| Leading Goal Scorer |
Noel Ellerton |
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Serbian White Eagles |
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| Goalkeeper of the Year |
Alex Pereski |
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Serbian White Eagles |
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Adam Orologio |
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Woodbridge Azzurri |
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| MVP of the Year |
Slobodan Djokic |
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Serbian White Eagles |
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| Rookie of the Year |
Adam Aprile |
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Woodbridge Azzurri |
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| OSL
South Region |
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| Leading Goal Scorer |
Krzysztof Bajewicz |
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Lakeshore United |
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| Goalkeeper of the Year |
Heiko Bauer |
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HNNK Zagreb |
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| MVP of the Year |
Richard West |
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Ebony Jrs |
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| Rookie of the Year |
Andrew Evans |
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Ebony Jrs |
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| OSL Provincial East Under 21 |
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| Leading Goal Scorer |
David Patullo |
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Vaughan Shooters |
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| Goalkeeper of the Year |
Joey DuDumas |
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Vaughan Azzurri |
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| MVP of the Year |
Kingsley Behome |
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Armour Heights |
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| OSL Provincial West Under 21 |
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| Leading Goal Scorer |
Evan James |
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Oakville SC |
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| Goalkeeper of the Year |
Robert Mienert |
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Oakville SC |
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| MVP of the Year |
Evan James |
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Oakville SC |
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| OSL Central Region Under 21 |
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| Leading Goal Scorer |
Jesse McIlmoyle |
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Peterborough City |
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| Goalkeeper of the year |
Dan Atkinson |
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Peterborough City |
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| MVP of the year |
Josh Elgeti |
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Peterborough City |
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| OSL South Region Under 21 |
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| Leading Goal Scorer |
Thomas McLean |
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Byrst F.A. |
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| Goalkeeper of the year |
Matthew Mayer |
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PCC Supersonics |
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| MVP of the year |
Alex Doma |
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PCC Supersonics |
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| OSL MJ District East |
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| Leading Goal Scorer |
Orest Arendacz |
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USC Karpaty |
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| Goalkeeper of the Year |
Adam Farr |
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Whitby Iroquois |
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| MVP of the Year |
Chris Giamou |
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Whitby Iroquois |
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| OSL MJ District West |
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| Leading Goal Scorer |
Theo Modeste |
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ACU Jaguars |
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| Goalkeeper of the Year |
Kevin Christie |
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ACU Jaguars |
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Matt Voltsis |
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| MVP of the Year |
Theo Modeste |
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ACU Jaguars |
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| ALF
BEESE CUP |
Croatia Hamilton |
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| FRANK DOCHERTY CUP |
Serbian White Eagles |
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| GEORGE FINNIE CUP |
ACU Jaguars |
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| OSL Playoff Champions |
GS United |
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| COACHES |
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| OSL Provincial |
Ronnie Davidson |
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Croatia Hamilton |
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| OSL Regional |
Scott Gardner |
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Toronto Celtic |
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| OSL Under 21 |
Neil Brown |
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Oakville SC |
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| OSL MJ District |
Angelo Leewo |
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ACU Jaguars |
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| DISCIPLINE |
Toronto Blues |
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