| Date | Transaction |
| 02-28-2013 | Roger Olive has retired from the Cleveland Ironmen. |
| 01-28-2013 | The Cleveland Ironmen have acquired Roger Olive from the waiver wire; however, as he was traded or waived after the deadline and has not spent a full week on the wire, he will not be eligible for the postseason. |
| 01-28-2013 | The Cleveland Ironmen have waived Roger Olive. |
| 01-28-2013 | The Cleveland Ironmen have acquired Roger Olive from the waiver wire. |
| 09-09-2012 | The Cleveland Ironmen have automatically waived Roger Olive to comply with the 53-man roster limit. |
| 09-03-2012 | The Cleveland Ironmen have acquired Roger Olive from the waiver wire. |
| 09-03-2012 | The Cleveland Ironmen have waived Roger Olive. |
| 09-03-2012 | The Cleveland Ironmen have acquired Roger Olive from the waiver wire. |
| 09-03-2012 | The Cleveland Ironmen have waived Roger Olive. |
| 09-03-2012 | The Cleveland Ironmen have moved Andy Ballantine, Dick Himes, and Terry Falcon to the active roster. The Cleveland Ironmen have moved Moe Racine, Roger Olive, and Joe Lukens to the inactive roster. |
| 08-06-2012 | The Cleveland Ironmen have moved Mike LaHood, Herbie Crockett, Jesse Owens, Roger Olive, Dave Munchak, Marmaduke Trent, Glen Ray Hines, David Holmes, Bruce Landon, Bill Orduna, Ray Moody, Ed Cotton, Moe Racine, Grant Lee, Delroy Wilma, and Tom Mandarich to the active roster. The Cleveland Ironmen have moved Andy Ballantine, Gene Krupa, Lionel Taylor, Dickie Post, Warren Wells, John Mackey, Ross Uhlenhake, Roger Pillath, Fair Hooker, Dick Himes, Don Poppowell, Bruce Tarbox, Terry Falcon, Roman Gabriel, Leland Glass, and Bobby McCrory to the inactive roster. |
| 01-30-2012 | The Cleveland Ironmen have acquired Roger Olive from the waiver wire; however, as he was traded or waived after the deadline and has not spent a full week on the wire, he will not be eligible for the postseason. |
| 01-30-2012 | The Cleveland Ironmen have waived Roger Olive. |
| 01-30-2012 | The Cleveland Ironmen have acquired Roger Olive from the waiver wire. |
| 09-18-2011 | The Cleveland Ironmen have automatically waived Roger Olive to comply with the 53-man roster limit. |
| 09-12-2011 | The Cleveland Ironmen have acquired Roger Olive from the waiver wire. |
| 09-12-2011 | The Cleveland Ironmen have waived Roger Olive. |
| 09-12-2011 | The Cleveland Ironmen have acquired Roger Olive from the waiver wire. |
| 09-05-2011 | The Miami Cobras have waived Roger Olive. |
| 09-06-2010 | The Miami Cobras have moved Roger Olive to the active roster. |
| 09-06-2010 | Trade #84177 has been completed between the Tulsa Osage and the Miami Cobras. The Miami Cobras receive Roger Olive (G), Draft Pick - 2011 Round 3 (TUL) from the Tulsa Osage in exchange for Pete Vollers (T). |
| 08-09-2010 | The Tulsa Osage have moved Keith Lamme, John Williams, Danzell Milne, and John Carolan to the active roster. The Tulsa Osage have moved Wes Ostendarp, Brian Krupa, Roger Olive, and Hal Holmes to the inactive roster. |
| 09-07-2009 | The Tulsa Osage have moved Tom Latzke, Brian Krupa, Albert Mathews, Roger Olive, Rick Bond, Roy Zaeske, Tony Lemek, and Jarrod Wesbecher to the active roster. The Tulsa Osage have moved John Spilis, Tom Johnson, Elmer Evans, John Griffith, Carl Enderle, Pete Smith, and Monk Johnson to the inactive roster. |
| 08-10-2009 | The Tulsa Osage have moved Danny Bauer, John Spilis, Carl Enderle, Elmer Evans, Pete Smith, William Jackson, Boyce Guess, and Scot Urevig to the active roster. The Tulsa Osage have moved Jarrod Wesbecher, Roger Olive, Rick Bond, Roy Zaeske, Tom Latzke, Darry Dangle, and Brian Krupa to the inactive roster. |
| 09-03-2007 | The Tulsa Osage have moved Ben Hennings, Roger Olive, and Danny Bauer to the active roster. The Tulsa Osage have moved Mickey Martin, Jay Gentry, and George Davis to the inactive roster. |
| 08-12-2007 | The Tulsa Osage have moved Mickey Martin, Robert Sullivan, Harry Pittman, and Carlos Smagala to the active roster. The Tulsa Osage have moved Zach Dixon, Ben Hennings, Steve Steinmetz, and Roger Olive to the inactive roster. |
| 11-27-2006 | The Tulsa Osage have moved Roger Olive, Roy Zaeske, and Mike Gibson to the active roster. The Tulsa Osage have moved Orantes Waters, Ralph Norton, and Brett Del Bello to the inactive roster. |
| 11-12-2006 | The Tulsa Osage have moved Orantes Waters and Ralph Norton to the active roster. The Tulsa Osage have moved Roger Olive and Roy Zaeske to the inactive roster. |
| 11-12-2006 | Roger Olive of the Tulsa Osage is injured with an ankle ligament sprain and is expected to be out for approximately 21 days. |
| 12-22-2002 | Roger Olive of the Tulsa Osage is injured with a knee derangement and is expected to be out for approximately 18 days. |
| 11-01-1998 | The Tulsa Osage have moved Roger Olive to the active roster. The Tulsa Osage have moved Albert Mathews to the inactive roster. |
| 09-21-1998 | The Tulsa Osage have moved Robert Bryant to the active roster. The Tulsa Osage have moved Roger Olive to the inactive roster. |
| 09-20-1998 | Roger Olive of the Tulsa Osage is injured with a lower leg fracture and is expected to be out for approximately 48 days. |
| 08-10-1998 | The Tulsa Osage have moved Albert Mathews, Roger Olive, Mario Miller, Rick Bond, and Bob Davis to the active roster. The Tulsa Osage have moved Mike Olsen, Roger Riggins, Firpo Whitten, Larry Wolfley, and Robert Bryant to the inactive roster. |
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