| Date | Transaction |
| 02-28-2005 | Raymond Simington has retired from football. |
| 01-19-2003 | The Edmonton Frostbite have moved Lindsay Greenwood to the active roster. The Edmonton Frostbite have moved Ross Oldham to the inactive roster. |
| 01-19-2003 | The Edmonton Frostbite have waived Raymond Simington. |
| 01-19-2003 | The Edmonton Frostbite have moved Izell Ragusa and Rod Stolberg to the active roster. The Edmonton Frostbite have moved Raymond Simington and Jim Cooper to the inactive roster. |
| 01-06-2003 | The Edmonton Frostbite have moved Raymond Simington to the active roster. The Edmonton Frostbite have moved Izell Ragusa to the inactive roster. |
| 01-06-2003 | The Edmonton Frostbite have acquired Raymond Simington from the waiver wire. |
| 09-02-2002 | The Tulsa Osage have moved Moses Winfrey, Mike Olsen, George Panciera, Steve Baumgartner, Ben Hennings, and Bob Johnson to the active roster. The Tulsa Osage have moved Dana Carroll, Monk Johnson, and David Adams to the inactive roster. |
| 09-02-2002 | The Tulsa Osage have waived Raymond Simington. |
| 08-11-2002 | The Tulsa Osage have placed Raymond Simington on the trade block. |
| 08-05-2002 | The Tulsa Osage have moved John Sabados, James Magerkurth, Monk Johnson, Gary Carroll, David Holmes, Dana Carroll, and Steve Atcheson to the active roster. The Tulsa Osage have moved Mike Olsen, George Panciera, Bob Johnson, Raymond Simington, Moses Winfrey, Steve Baumgartner, Ben Hennings, Tony Linden, and Tony Burns to the inactive roster. |
| 09-04-2000 | The Tulsa Osage have moved Raymond Simington, Mike Olsen, Dave Suggs, and Larry Wolfley to the active roster. The Tulsa Osage have moved Dennis Kelly, Jack Seborg, Monk Johnson, and Bob Davis to the inactive roster. |
| 08-07-2000 | The Tulsa Osage have moved Jack Seborg, Mario Miller, Mark Stribling, and Bob Davis to the active roster. The Tulsa Osage have moved Raymond Simington, Mike Olsen, Bill Lynch, and Larry Wolfley to the inactive roster. |
| 09-06-1998 | The Tulsa Osage have moved Raymond Simington, Henry Tanner, Mike Olsen, Roger Riggins, and Tra'Davious Young to the active roster. The Tulsa Osage have moved Benny Rizzo, Jack Seborg, Keith Carter, Mario Miller, and Babe Duncan to the inactive roster. |
| 12-29-1997 | The Tulsa Osage have moved Keith Carter to the active roster. The Tulsa Osage have moved Raymond Simington to the inactive roster. |
| 12-28-1997 | Raymond Simington of the Tulsa Osage is injured with a shoulder muscle strain and is expected to be out for approximately 11 days. |
| 08-10-1992 | The Tulsa Osage have moved Raymond Simington, Bill Lynch, Roger Riggins, Glen DeLuca, Scott Jones, Robert Bryant, Leon Hester, Ralph Bruggers, and Larry Young to the active roster. The Tulsa Osage have moved Bill Franco, Henry Tanner, David Joseph, Cully Elam, Vince Armstrong, Tony Morgan, John Jones, Grant Collins, and Buckets Curtis to the inactive roster. |
Wide Receiver