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Proving Ground 2009: Night One featured professional wrestling matches, which involved different wrestlers from pre-existing scripted feuds, plots, and storylines that played out on ROH's television programs. Wrestlers portrayed villains or heroes as they followed a series of events that built tension and culminated in a wrestling match or series of matches.
- Dark match: Alex Payne defeats Wes Eskimo
- Dark match: The British Lions (Chris Gray & Tommy Taylor) defeat The Heartbreak Express (Phil Davis & Sean Davis)
- Brad Attitude defeats Shawn Osbourne (7:31)
- Bison Smith defeats Sal Rinauro (2:11)
- Bobby Dempsey, Erick Stevens & Roderick Strong defeat Chasyn Rance, Kenny King & Rhett Titus (11:33)
- Austin Aries defeats Necro Butcher (12:53)
- Bryan Danielson & Jerry Lynn defeat The Age Of The Fall (Delirious & Jimmy Jacobs) (17:04)
- Nigel McGuinness defeats Brent Albright (18:18)
- El Generico & Kevin Steen defeat The Dark City Fight Club (Jon Davis & Kory Chavis) (12:09)
- Tyler Black defeats Davey Richards (w/ Larry Sweeney) (17:33)