Was a single trophy really important enough to spawn two different discussions?
Sometimes, I put in details solely because it adds a touch of realism or detail to a panel. It seemed like it says something about the character if he didn't win every single time; it says that he's good, but not unbeatable. However, I can assure you there is no more importance to it than that, nor will it ever be mentioned again.
Not everything has a story attached to it, or at least, not a story worth telling.