What's the most iconic contest match?

Yeah, from a "outside of GameFAQs" standpoint it's L-Block > Link and I don't even know if it's particularly close.

Outside of Board 8 but still on the rest of the site it might somehow be Cloud > Link or FFVII > OoT just because for the longest time (maybe even still?) you'd have people from off the board drop in and whine that "Final Fantasy always wins" and that's like the only match that I think that should be coming from. but strong emphasis on "should" there because i don't really know if logic played any part in that

For inside Board 8 I'd say the shortlist is (leaving off 2002 because that was before I arrived):

Mario/Crono II
Mario/Samus
Link/Shepard/Draven
L-Block
Magus/Knuckles

Probably missing some obvious ones but those felt like some of the bigger moments for the board's... culture/view of contests IMO. I guess a more "recent" one would be some of the "plucky underdog pokemon" matches.