| Date | Transaction |
| 02-28-1992 | Bob Cupp has retired from football. |
| 09-02-1990 | The Pittsburgh Steel Curtain have waived Bob Cupp. |
| 08-06-1990 | The Pittsburgh Steel Curtain have moved Doug Turnbow and Win Bain to the active roster. The Pittsburgh Steel Curtain have moved Bob Cupp and Gary Ellis to the inactive roster. |
| 09-04-1989 | The Pittsburgh Steel Curtain have moved Bob Cupp to the active roster. The Pittsburgh Steel Curtain have moved Bart Norby to the inactive roster. |
| 09-04-1989 | The Pittsburgh Steel Curtain have acquired Bob Cupp from the waiver wire. |
| 08-28-1989 | The Phoenix Reapers have waived Bob Cupp. |
| 01-02-1989 | The Phoenix Reapers have moved Bob Cupp to the active roster. The Phoenix Reapers have moved David Carr to the inactive roster. |
| 01-02-1989 | The Phoenix Reapers have acquired Bob Cupp from the waiver wire. |
| 12-19-1988 | The Saskatchewan Chimeras have waived Bob Cupp. |
| 12-12-1988 | The Saskatchewan Chimeras have moved Bob Cupp and Dozer Brown to the active roster. The Saskatchewan Chimeras have moved Rembrandt Litman to the inactive roster. |
| 11-21-1988 | The Saskatchewan Chimeras have acquired Bob Cupp from the waiver wire. |
| 10-31-1988 | The Winnipeg Jets have moved Jonathan Sapolu to the active roster. The Winnipeg Jets have moved Floyd Joelson to the inactive roster. |
| 10-31-1988 | The Winnipeg Jets have waived Bob Cupp. |
| 10-10-1988 | The Winnipeg Jets have moved Jermaine Kuffel, Ted Montgomery, Harold Bennett, Pat Mitchell, Win Garrett, and Howie Henke to the active roster. The Winnipeg Jets have moved Gerald Kent, Bob Cupp, Randy Harper, Tom Jones, Phil Reed, and Jeff Garnes to the inactive roster. |
| 09-04-1988 | The Winnipeg Jets have moved Billy Crabtree, Joe Goode, Travis Dwyer, Rube Nicholson, Cody Marshall, Levi Graham, Tom Jones, Bob Cupp, Drake Kasady, Wayland Davis, Walt Mills, Ray Alberts, and Win Garrett to the active roster. The Winnipeg Jets have moved Don Ward, Don Williams, Larry Bruno, Jim Ward, Pat Mitchell, Bosh Brunson, Ralph Moore, George Perko, and Harold Bennett to the inactive roster. |
| 08-14-1988 | The Winnipeg Jets have removed Bob Cupp from the trade block. |
| 08-08-1988 | The Winnipeg Jets have placed Bob Cupp on the trade block. |
| 02-08-1988 | The Winnipeg Jets have moved Bob Cupp to the inactive roster. |
| 11-30-1986 | Bob Cupp of the Winnipeg Jets is injured with a quadricep contusion and is expected to be out for approximately 5 days. |
| 01-03-1982 | The Winnipeg Jets have moved Elbert Rouson, Billy Crabtree, Mike Stephens, Larry Hopkins, Spain Laughlin, Ron Wood, Tom Scott, Bob Cupp, Wayland Davis, Robert Cowsette, Charlie Quillen, Earl Wilson, and Darren Washington to the active roster. The Winnipeg Jets have moved Mike Williams, Cliff Jones, Benny Reynolds, Joe Parker, Walt Burt, Bobby Jordan, Jesse Short, and Michael Mills to the inactive roster. |
| 12-28-1981 | The Winnipeg Jets have moved Cliff Jones, Mike Williams, Benny Reynolds, Bobby Jordan, Walt Burt, Jesse Short, and Joe Parker to the active roster. The Winnipeg Jets have moved Robert Cowsette, Charlie Quillen, Tom Scott, Earl Wilson, Bob Cupp, Darren Washington, Elbert Rouson, Larry Hopkins, Ron Wood, Spain Laughlin, Wayland Davis, and Billy Crabtree to the inactive roster. |
| 08-04-1980 | The Winnipeg Jets have moved Walt Burt, Steve McNally, Bob Cupp, Win Garrett, Chal Jolitz, and Johnny Hall to the active roster. The Winnipeg Jets have moved Ron Romney and Ed Clifton to the inactive roster. |
Defensive End