The matches I am thinking of are usually momentous ones, where there's a lot on the line and/or uncharted territory for one player.
Shapo v Nadal at 2022 AO was his match to lose, ditto Medvedev at same event and neither has been the same since. Tpas v Djoko, Musetti v Djoko...those would have been the biggest wins of their careers and would have been regarded as proper ascendancies for players we mostly think are potential greats...like Federer taking out Sampras, as opposed to flukes like Nardi's comical upset of Djoko...and they crumbled under the pressure
This Tiafoe match, in retrospect, was even bigger than it seemed at the time. Tiafoe at that time had an argument for being the great American hope after his huge win over Rafa at USO. And was pretty much the only young American black player that had captured our imagination since Blake. He lost both of those belts to Shelton that day