| # | Date | Promotion | Match |
| 1 | 19.12.2009 |  |
The Embassy (Bison Smith & Erick Stevens) defeat Bobby Dempsey & Delirious (9:41) ROH Final Battle 2009 - Pay Per View @ Manhattan Center in New York City, New York, USA |
| 2 | 05.12.2009 | |
Dark: Grizzly Redwood & Pelle Primeau defeat Alex Payne & Bobby Dempsey ROH Reverse The Curse - Dark Match @ Frontier Fieldhouse in Chicago Ridge, Illinois, USA |
| 3 | 14.11.2009 | |
Dark: Alex Payne & Bobby Dempsey defeat Ethan Page & Michael Von Payton ROH The Omega Effect - Dark Match @ International Centre in Mississauga, Ontario, Canada |
| 4 | 13.11.2009 | |
Dark: Bobby Dempsey defeats ??? ROH Aries Vs. Richards - Dark Match @ Rock Financial Showplace in Novi, Michigan, USA |
| 5 | 07.11.2009 | |
Bobby Dempsey defeats Tony Kozina (4:11) ROH Boiling Point 2009 - Event @ Inman Sports Club in Edison, New Jersey, USA |
| 6 | 06.11.2009 |  |
Dark: Bobby Dempsey & Lance Bravado defeat Gino Giovanni & Tony Nese ROH on HDNet #41 - Dark Match @ The Arena in Philadelphia, Pennsylvania, USA |
| 7 | 05.11.2009 | |
Dark: Bobby Dempsey & Grizzly Redwood defeat Andy Ridge & John Kermon ROH on HDNet #37 - Dark Match @ The Arena in Philadelphia, Pennsylvania, USA |
| 8 | 10.10.2009 | |
Dark: Bobby Dempsey, Kyle O'Reilly & Ricochet defeat Aaron Scott, Shawn Schultz & Tommy Mercer ROH Survival Of The Fittest 2009 - Dark Match @ Indiana State Fairgrounds in Indianapolis, Indiana, USA |
| 9 | 09.10.2009 | |
Dark: Alex Payne, Bobby Dempsey & Mike Sydal defeat Aaron Scott, Muscle Machine & Shawn Schultz ROH Clash Of The Contenders - Dark Match @ One Gateway Center in Collinsville, Illinois, USA |
| 10 | 25.09.2009 | |
The Dark City Fight Club (Jon Davis & Kory Chavis) defeat Alex Payne & Bobby Dempsey (6:41) ROH The Final Countdown Tour - Tag 3 - Event @ Boston University in Boston, Massachusetts, USA |
| 11 | 19.09.2009 | |
Bobby Dempsey & Brent Albright defeat The House Of Truth (Christin Able & Josh Raymond) (12:24) ROH The Final Countdown Tour - Tag 2 - Event @ Frontier Fieldhouse in Chicago Ridge, Illinois, USA |
| 12 | 18.09.2009 | |
Dark: Bobby Dempsey & Tim Donst defeat Andy Ridge & Jordan McEntyre ROH The Final Countdown Tour - Tag 1 - Dark Match @ Montgomery County Fairgrounds in Dayton, Ohio, USA |
| 13 | 11.09.2009 | |
Dark: Andy Ridge & Bobby Dempsey defeat Bobby Shields & Bruno Marciano ROH on HDNet #34 - Dark Match @ The Arena in Philadelphia, Pennsylvania, USA |
| 14 | 10.09.2009 | |
Chris Hero defeats Bobby Dempsey (3:20) ROH on HDNet #33 - TV-Show @ The Arena in Philadelphia, Pennsylvania, USA |
| 15 | 15.08.2009 | |
Dark: Bobby Dempsey & Tony Dees defeat Bruno Marciano & Gino Giovanni ROH on HDNet #28 - Dark Match @ The Arena in Philadelphia, Pennsylvania, USA |
| 16 | 14.08.2009 | |
Dark: ??? & Bobby Dempsey defeat ??? & ??? ROH on HDNet #25 - Dark Match @ The Arena in Philadelphia, Pennsylvania, USA |
| 17 | 25.07.2009 | |
Dark: Alex Payne, Andy Ridge & Bobby Dempsey defeat Ethan Page & The Flatliners (Asylum & Matt Burns) ROH Death Before Dishonor VII - Tag 2 - Dark Match @ Ted Reeve Arena in Toronto, Ontario, Canada |
| 18 | 24.07.2009 | |
Dark: Alex Payne & Bobby Dempsey defeat The Flatliners (Asylum & Matt Burns) ROH Death Before Dishonor VII - Tag 1 - Dark Match @ Ted Reeve Arena in Toronto, Ontario, Canada |
| 19 | 27.06.2009 | |
Dark: Bobby Dempsey & Kawada defeat Andy Ridge & Sonny Samson ROH End Of An Age - Dark Match @ Frontier Fieldhouse in Chicago Ridge, Illinois, USA |
| 20 | 20.06.2009 | |
Dark: Atsushi Sawada & Bobby Dempsey defeat The Set (J-Sin & Lance Lude) ROH on HDNet #22 - Dark Match @ The Arena in Philadelphia, Pennsylvania, USA |
| 21 | 19.06.2009 | |
Dark: Bobby Dempsey defeats Andy Ridge ROH on HDNet #19 - Dark Match @ The Arena in Philadelphia, Pennsylvania, USA |
| 22 | 12.06.2009 | |
Dark: Atsushi Sawada, Bobby Dempsey & John Kermon defeat Bobby Shields & The Set (J-Sin & Lance Lude) ROH Contention - Dark Match @ Sports Network & Fitness in Manassas, Virginia, USA |
| 23 | 09.05.2009 | |
Dark: Bobby Dempsey & Matt Taven defeat Gino Giovanni & Jaleel Patel ROH Validation - Dark Match @ Inman Sports Club in Edison, New Jersey, USA |
| 24 | 08.05.2009 | |
Dark: Alex Payne & Bobby Dempsey defeat Brandon Day & Ray Kejimura ROH Never Say Die - Dark Match @ Boston University in Boston, Massachusetts, USA |
| 25 | 25.04.2009 | |
Dark: Bobby Dempsey defeats Steve Molinski ROH The Homecoming 2009 - Dark Match @ Frontier Fieldhouse in Chicago Ridge, Illinois, USA |
| 26 | 18.04.2009 | |
Dark: Christin Able & Josh Raymond defeat Bobby Dempsey & Grizzly Redwood ROH Tag Title Classic - Dark Match @ Markham Fair in Markham, Ontario, Canada |
| 27 | 10.04.2009 | |
Bobby Dempsey defeats Sal Rinauro (0:47) ROH on HDNet #12 - TV-Show @ The Arena in Philadelphia, Pennsylvania, USA |
| 28 | 09.04.2009 | |
Dark: Bobby Dempsey defeats Ninja Brown ROH on HDNet #7 - Dark Match @ The Arena in Philadelphia, Pennsylvania, USA |
| 29 | 04.04.2009 | |
Dark: Alex Payne, Andy Ridge & Bobby Dempsey defeat Darin Childs, Don Juan & Mike Dell ROH Take No Prisoners 2009 - Dark Match @ George R. Brown Convention Center in Houston, Texas, USA |
| 30 | 21.03.2009 | |
Bobby Dempsey defeats Adam Pearce (0:25) ROH 7th Anniversary Show - Event @ Hammerstein Ballroom in New York City, New York, USA |
| 31 | 13.03.2009 | |
Sweet 'n' Sour Inc. (Chris Hero, Davey Richards & Eddie Edwards) defeat Bobby Dempsey, El Generico & Kevin Steen (16:23) ROH Stylin' & Profilin' - Event @ Gateway Center in Collinsville, Illinois, USA |
| 32 | 01.03.2009 | |
Bobby Dempsey defeats Orange Cassidy (0:23) ROH on HDNet #5 - TV-Show @ The Arena in Philadelphia, Pennsylvania, USA |
| 33 | 28.02.2009 | |
Dark: Andy Ridge & Bobby Dempsey defeat Bobby Shields & Ernie Osiris (3:29) ROH on HDNet #1 - Dark Match @ The Arena in Philadelphia, Pennsylvania, USA |
| 34 | 27.02.2009 | |
Kenny King & Rhett Titus defeat Bobby Dempsey & Erick Stevens (12:27) ROH Eliminating The Competition - Event @ Danbury Police Athletic League Building in Danbury, Connecticut, USA |
| 35 | 07.02.2009 | |
Dark: The YRR (Chasyn Rance & Sal Rinauro) defeat Bobby Dempsey & Ninja Brown ROH Proving Ground 2009 - Tag 2 - Dark Match @ Orlando Downtown Recreation Complex in Orlando, Florida, USA |
| 36 | 06.02.2009 | |
Bobby Dempsey, Erick Stevens & Roderick Strong defeat Chasyn Rance, Kenny King & Rhett Titus (11:33) ROH Proving Ground 2009 - Tag 1 - Event @ Coral Springs Gymnasium in Coral Springs, Florida, USA |
| 37 | 31.01.2009 | |
Steel Cage War: Ace Steel, Brent Albright, Erick Stevens, Jay Briscoe & Roderick Strong defeat Sweet 'n' Sour Inc. (Adam Pearce, Bobby Dempsey, Davey Richards, Eddie Edwards & Tank Toland) (17:24) ROH Caged Collision - Event @ Frontier Fieldhouse in Chicago Ridge, Illinois, USA |
| 38 | 17.01.2009 | |
Dark: Bobby Dempsey defeats Orange Cassidy ROH Injustice II - Dark Match @ Inman Sports Club in Edison, New Jersey, USA |
