Starcraft > Halo (2004)
Cloud > Link (2003)
Zelda > Mario (2018)
(Link >) Vincent > Crono (> Zero) (2007)
Not including rallies since those are kinda a different category, but I understand if someone includes these. Also didn't really want to include 2002 matches since everything was new so we didn't really know what would happen.
"so is my word...It will not return to me empty, but will accomplish what I desire and achieve the purpose for which I sent it." - Isaiah 55:11