Duran was an underdog for Buchanan, Leonard, Moore, & Barkley. I believe Holyfield was an underdog for Qawi 1, Douglas, Bowe 2, Tyson x2, & Rahman.
That's what I thought of on Duran also. I think that's also what got him the p4p pass other than one of,if not the best singular win in history over prime Leonard,he was set as the underdog for all 4,even vs Hagler where he loses,he still performed good as an underdog.
If we're including newspaper decisions, Soldier Bartfield beat the 14lbs heavier Harry Greb, as well as ATG WWs Jack Britton and Ted Kid Lewis, the latter twice. I suspect 2 x wins over the 10-13lbs heavier Al McCoy and borderline great Jimmy Duffy were also considered upsets.
Jim Braddock scored a string of upsets on his way to getting both of his title shots, then eventually pulled off 1 of the most celebrated upsets in boxing history over Baer.