| Date | Transaction |
| 02-28-2019 | Tony Simon has retired from football. |
| 09-12-2016 | The Winnipeg Amish have waived Tony Simon. |
| 09-04-2016 | The Winnipeg Amish have moved Chris Tucker, LeFrancis Baumgartner, Frank Davis, Fritz Reynolds, Frank Mintun, Chuck Clay, Chuck Cosgrove, Joe Culver, Mark Wilson, Daryl Hagerty, and John Hasselbeck to the active roster. The Winnipeg Amish have moved Tony Simon, Frankie Garrison, Chuck Ryan, John Blumer, Al Graham, Paul Robinson, Ziggy Lewis, Mike Smith, and Gerry Gardner to the inactive roster. |
| 08-28-2016 | The Winnipeg Amish have moved Tony Simon, Ziggy Lewis, and Asti LaVista to the active roster. |
| 08-14-2016 | The Winnipeg Amish have placed Tony Simon on the trade block. |
| 01-18-2016 | The Winnipeg Amish have moved Clark Carr, Bill Gonzalez, Paul Robinson, Gerry Gardner, and Ed McBride to the active roster. The Winnipeg Amish have moved Tony Simon, Chris Tucker, Chuck Clay, Marlboro Miles, Mark Wilson, Ron Bauman, Daryl Hagerty, and John Hasselbeck to the inactive roster. |
| 01-10-2016 | Tony Simon of the Winnipeg Amish is injured with a knee contusion and is expected to be out for approximately 7 days. |
| 09-06-2015 | The Winnipeg Amish have moved Ziggy Lewis, Ron Bauman, and Tony Simon to the active roster. The Winnipeg Amish have moved Brock Cook, Bail Organa, and John Blumer to the inactive roster. |
| 05-03-2015 | The Winnipeg Amish have moved Brandon Haak, Warren Spinks, Reggie Giancanelli, Barry Raskowski, Ed Redding, Darren Marks, and Jumbo Hodge to the active roster. The Winnipeg Amish have moved Tony Simon, Chris Tucker, Chuck Clay, Marlboro Miles, Joe Culver, Mark Wilson, Ron Bauman, Daryl Hagerty, and John Hasselbeck to the inactive roster. |
| 08-31-2014 | The Winnipeg Amish have moved Tony Simon, Chris Tucker, Chuck Clay, Ed Lorick, Mark Wilson, Steve Strom, Ron Bauman, Chris Judie, Daryl Hagerty, John Hasselbeck, and Marcus Abrams to the active roster. The Winnipeg Amish have moved Brandon Haak, Chuck Ryan, Reggie Giancanelli, Barry Raskowski, Bud Walters, Weldon Trammell, and Mike Green to the inactive roster. |
| 04-27-2014 | The Winnipeg Amish have moved Keith Thomas to the active roster. The Winnipeg Amish have moved Tony Simon, Chris Tucker, Scott Ciccolella, Chuck Clay, Ben Kenobi, Mark Wilson, Ron Bauman, and Chris Judie to the inactive roster. |
| 10-14-2007 | The New England Amish have moved Tony Simon to the active roster. The New England Amish have moved Charley Williams to the inactive roster. |
| 09-16-2007 | The New England Amish have moved Charley Williams, Reggie Feather, and Greg Bartlett to the active roster. The New England Amish have moved Tony Simon, Jerry Moynihan, and Greg Krutko to the inactive roster. |
| 09-16-2007 | Tony Simon of the New England Amish is injured with a shoulder dislocation and is expected to be out for approximately 34 days. |
| 08-06-2007 | The New England Amish have moved Tony Simon, Chris Tucker, Jerry Moynihan, and Joe Culver to the active roster. |
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