February 13, 2006: Cowboy Bob Orton was released from the World Wrestling Entertainment.
May 26, 2007 – OSWA: WWE Legend “Cowboy” Bob Orton defeated NWX Member Kris Synz in Woodriver, Illinois ..
Chris Lemp a.k.a. Kris Synz wrote: I am writing you to give some insight I guess you could say to my match with “Cowboy” Bob Orton Jr. from May 26th, 2007. In the “Cowboy” Bob Orton Jr. article (below), Charles Wilson wrote about Orton’s kneedrop, let me tell you that move still hurts today. After taking 2 of them I had a knot on the side of my head. But I wouldn’t of traded the expierence for anything. Bob was nothing but curtious all night, and has a great sense of humor. Also he has no ego, which is a great thing for someone who so easily could have one.
August 2, 2008 – Full Throttle Wrestling: Bob Orton and The Searcher and Damian Blade defeated Scar and Xavier Frost and Max Archer
October 17, 2009 – Independent Hardcore Wrestling: “Bloody” Harker Dirge defeated Cowboy Bob Orton by disqualification.
Chuck STLHBKid wrote: It was a local indy show by IHW (Independent Hardcore Wrestling) in DUPO ILLINOIS, (Saturday Night 10/17/09) and the match was “Bloody” Harker Dirge vs. Cowboy Bob Orton for the PWE Belt. Who comes out with Cowboy Bob Orton – his son!!! No, not Randy. but NATHAN ORTON! Stunning resemblance to Randy when he first entered WWE years ago, he escorted his dad to the ring and was at ringside for the match. Harker Dirge started to choke out Cowboy Bob Orton, when his son Nathan had enough, and out of no where – punted Harker in the head!!!!! The bell was rang and “Bloody” Harker Dirge retained the PWE Belt to take back to the Chicago area. Nathan was apologizing to his father over and over, and the crowd erupted a huge “ORTONS, ORTONS, ORTONS” chant!!! Post match backstage – Nathan was telling everyone that he had a total blast, and it was sooo much fun!!!!
October 2, 2010 – Independent Hardcore Wrestling: Bob Orton Jr. (59) defeated Brandon Graves in Red Bud, Illinois.
January 29, 2011 – Pro Wrestling Guerrilla: Bob Orton participated in a Legends Wrestle-Royale in Los Angeles, California.
Charles Wilson wrote: I ran across the listing for Bob jr. and noticed the overload of WWE stuff and how many matches he is listed as losing. Lemme tell ya’: Many will tell you the greatest World Tag Team Champions were the Andersons. Cannot argue that. But the greatest Tag Team ever was Bob Roop and Bob Orton jr. PERIOD! When Roop was faced with the task of branching out after being a single’s competitor for so long, he matched up with the likes of Killer Karl Krupp. *Ugh!* He partnered with some others and got nowhere. Then, in a bit of booking magic, someone paired Roop and Orton and the question became, “When is a pinning combination not a pinning combination?” Answer: When you’ve made the tag with your partner! Roop, ever the Greco-Roman master, would tag Orton and roll the opponent into a backslide. The fish would begin to try to roll out when Orton would jump about 27 feet high and bring a knee into his forehead. People in the stands just went berserk! Orton and Roop just seemed to have fun and they brought life to the Tag Team event when everyone else simply put up with it or used it as a set-up or grudge/revenge affair. I have truly not seen anything like those two – including the Andersons.