1st Place in Regular Season – Bobby Breen Memorial Trophy: Holy Cross/ The Dock
Rookie of the Year – Ed Moyst Award: Holy Cross/The Dock – Aaron Anstey
Top Defender – Jeff Babstock Award: St. Lawrence Labatt Laurentians – Clinton Edwards
Most Sportsmanlike Player – Jim Goff Award: Mount Pearl/That Pro Look/Molson – Ryan Caines
Golden Boot (Top Scorer) – Wils Molloy Award: Holy Cross/The Dock – Zack Wade
Coach of the Year – Phonse Warren Memorial Award: Holy Cross/The Dock – Jake Stanford
MVP – Regular Season – Dick Power Memorial Award: Holy Cross/The Dock – Zack Wade

2009 Molson Challenge Cup All -stars

All – Star Forwards (strikers) :

1. Corey Moore – Holy Cross/The Dock

2. Justin Pickford – Mt. Pearl/That Pro Look/Molson

All – Star Midfielders:

1. Rudy Norman – St.Lawrence Labatt Laurentians

2. Zack Wade – Holy Cross/The Dock

3. Shane Antle – Mt. Pearl/That Pro Look/Molson

4. Paul Slaney – St.Lawrence Labatt Laurentians

All – Star Fullbacks :

1. Andrew Murphy – Mt. Pearl/That Pro Look/Molson

2.Jon Kelly – Mt. Pearl/That Pro Look/Molson

3.Clinton Edwards – St.Lawrence Labatt Laurentians

4. Kevin Oram – Western United FC

All – Star Goalie :

Scott Edwards – Holy Cross/The Dock