Hollyfield vs Tyson I was only a kid at the time and asked my Dad to put my pocket money on bet for Hollyfield to win. My Dad refused as he thought Hollyfield stood no chance. I still gloat about this to him. Also another one I enjoyed was Groves vs Eubank. Overheard my boss speaking to colleague saying how "Eubank will batter Groves" I butted in and said "no way" and we made a bet. Joyce who was a large underdog against Dubois. Won a bet and seeing Warren's face was Priceless.
Bivol vs Canelo is one. That flurry Bivol threw at him in round 3 was just on point. It was obvious Canelo was confused and frightened as he panic blocked, still getting caught clean with a few hits and ended up backing off. I think it was at that moment his confidence dropped as he realized the kind of beatdown he was in for. Although if I had to pick one not listed on the poll, undoubtedly it'd be AJ vs Ruiz. Round 3 was so impressive with the knockdowns that a lot of people consider that to be when the heavyweight division came back to life.
It's not recent but I've got to give a shoutout to Corrie Sanders unforeseen destruction of Wlad K. Browne over Fa was a huge surprise, not sure if satisfying.
Side note I know bivol Schooling Canelo is a fan / hater favorite, especially on this site. & yes technically it was an upset as far as betting odds go. But for a hardcore boxing site such as this - is it really an truly an upset? not in my eyes anyway - saw it as 50/50 As an optimistic Mexican.
Ruiz beating Joshua and making him quit was far more satisfying than the other three options. Usyk beating Joshua was a no brainier anyway to be honest and it was no upset imo .