Joe Louis vs. Rocky Marciano Muhammad Ali vs Larry Holmes Jack Johnson vs Jess Willard Mike Tyson vs Lennox Lewis Riddick Bowe vs Andrew Golota II Evander Holyfield vs James Toney Max Schmeling vs Joe Louis II (For German fans)
I presume your not including fatalities. I'll go for Conteh vs Saad Muhammad 2 I think John was actually shot before the first fight but managed to put on a last hurrah. When he came back after this fight he was on a local Liverpool news tv programme talking about the loss and he literally broke down. Very sad!
at the time I felt very bad for McClellen also felt really totally gutted when I heard about Mason recently saddest boxing stories for me are the Johnny Bratton Story and the combined tale of Bat nelson and Ad Wolgast, closely followed by the whole Luis Resto Billy Collins mess
On a more serious note, of course, the 3rd Griffith-Paret fight....and the aforementioned Collins-Resto crime.
I think this was 2 but it might have been 3-it was an amazing moment caught on film, the angle at which we saw Morales squint as if weighing the options of continuing and whether he could win, while looking at his corner and father, before slightly shaking his head to himself, "it's not worth it", and then giving up.
Tyson-McBride comes to mind. Of course Holmes-Ali. The state of Meldrick Taylor. The state of Muhammad Ali. (these aren't moments, but sad nonetheless)
Arturo Gatti vs Floyd Mayweather Joey Gamache vs Arturo Gatti Willie Classen vs Wilford Scypion Jerry Quarry vs Ken Norton