Perhaps the most 'outstanding' award has to go to a Mr. Devaney who tackled a veteran of 83 recorded battes in his fist recorded pro battle... This encounter being at the Gaeity Theatre in Sydney.. around 1909. Unfortunately, the brilliance of this battle is tarnished by the name "JOE GRIM"... Worse still, Devaney lost over the 6 rounds..
LOL, yeah, I did not mention him by name because he always comes up on these threads, and is a bit cliche.
Here's one. Micheal Carbajal's pro debut was against Will Grigsby, who would go on to win a couple of jr. flyweight titles in his own right. Not a bad little fight, either, because while Carbajal was the clear winner, Grigsby had his moments in that contest.
It was Grisgsby second fight though.... It is like giving James Smith credit for fighting James Broad on his debut and beating a future world titlist in his second bout (Parkey). Or Virgil Hill fighting a future challenger of his 175lbs crown in his third fight (Vedder). Or Bowe beating Butler on his debut. Hindsight yes, it is a name, but at the time they meant little, indeed Carbajal went further back for having to fight a little on his debut. He was lucky to a point, that, that big 1988 Olympian bill, was completely overshadowed by a huge snow storm, and this Panamanian fella's ability to turn the clock back six years!
Actually, I remember Clancy saying that of the opponents that the Olympians were facing that Grigsby was the best of the bunch. And it was a pretty close fight for two rounds (Grigsby even kind of wobbled Carbajal in the second, if my memory serves me correctly), and even though Micheal dropped Steel to one knee and won a clear decision, you could tell even then that Grigsby had some talent and could go places himself if he just stuck to it.
And, of course, let's not forget that Rafael Marquez fought and lost to Victor Rabinales, a former bantamweight titlist in his pro debut Edit: Just saw that TBooze had mentioned this. Well, Manuel Ortiz lost to one Benny Goldberg twice, once in his pro debut, and then faced and defeated him in defence of his bantamweight title, so he certainly wasn't matched very easily either from the start.
Of course, Carbajal was matched tough. But I doubt anyone in his camp thought for a second that Grigsby would go on to do what he did. Because if they did, it was very poor matchmaking.
Duran also faced Carlos Mendoza in his debut, who would later be a very respectable conter at junior featherweight, going hard rounds with Wilfredo Gomez, at Gomez's peak.
Evander Holyfield took on a straight badass in Byarm. I've never seen a fighter look as good in a debut as Pernell Whitaker. He looked like he was a world champion already. Flawless performance, and even great fighters have only a handful of those over an entire career.