The closest I recall getting is Holyfield-Tyson I. Going in, people thought Holyfield was beyond shot and Tyson was resurgent. There were rumblings in the boxing press that Tyson might actually kill Holyfield. I remember thinking that Holyfield was a warrior and that he would offer some resistance to Tyson; that it wouldn't be as easy for Tyson as people thought. But I did not think Holyfield would win. I also predicted that Carl Williams would beat Tyson by controlling him with the jab from the outside. We knew Tyson was going through a lot of outside turmoil and not training as hard as he should. Of course that happened, but it wasn't pulled off by Carl Williams. I had to wait six months. Which I didn't predict. My grandfather claimed he knew Ali was going to beat Liston in February 1964. But my grandfather also had no memory of Frazier beating Ali in the FOTC. So I take his Ali-Liston claim with a grain of salt.
I actually did predict this. Yea it's hard to say what upsets I would have predicted retroactively. Maybe Ali-Liston
I was ridiculed when I predicted ...... Margarito over Cotto in Fight 1 Ibeabuchi over Tua Ibeabuchi over Byrd Paulie Ayala over Johnny Tapia It helps when you know the guys well before picking them
I do have a tendency to play devils advocate with friends and casuals to the point where I convince myself the underdog and unlikely winner I was defending for arguments sake should be favoured going in. Unsurprisingly it doesn’t work that often lol.
I picked George Foreman to beat Joe Frazier in 1973, I won $10.00. I also picked against George when he lost to Jimmy Young on March 17 1977, I won another $10.00.
Actual predictions I made BEFORE the fight (and often had friendly wagers on the result): Tyson to stop Spinks within 2 rounds chavez - whitaker to be a draw (I was right but I was wrong - whitaker won) Meldrick Taylor to beat Chavez (I was right, and then I was wrong, but only by a couple of seconds) Buddy McGirt over Simon Brown (very proud of this because McGirt was a 5 to 1 underdog) De la Hoya to stop Ruelas within 3 rounds bowe over holyfield I Tyson to stop Seldon in the 1st round Diego Corrales over Roberto Garcia de la Hoya over Quartey by decision Mercer over Morrison Holmes to last the distance with Mercer Lewis to decision Tua Holy not to be stopped by Tyson in their first fight Holyfield over Tyson II (Holy actually was the underdog) Tapia over Romero Carbajal over Gonzalez Tyson over Golota and that Andrew would find a way to quit and get out of the fight one way or the other de la Hoya over Trinidad (I was right, but the judges said I was wrong)
I remember picking McBride to beat Tyson. Knew Mike was done. I picked Joe Calzaghe go beat Jeff Lacy even won 15 bucks out of it.
I am trying to think of the ones I did predict. I called a few over the years. Foreman-Moorer Barrera-Prince Naseem Trinidad- De La Hoya Here is a doubly controversial one: Chavez-Taylor. I guess most of the boxing community do not think Chavez won it, but the result stands. It is also a bit of a odd mention because it started out being a pick-em, but, if I remember correctly, betting moved heavily towards Taylor before the fight.