Thing is, It kinda didn't. The Orange League that is. It didn't have any near as much weight to it - as far as the anime itself, and it's cast was concerned. Everything that that first win meant back then (and I do take it as his first win, fuck anyone who thinks any of the other fictional leagues are more 'real') was the audiences' reaction. I watched it back. It's good. A bit flaky with the pacing, and bullshit at times but yeah he got the win.
Kid me lapped every bit of that battle up though. And kid me would've been shaking in his spot when Pikachu double K-Os Zoroark. Type: Wild (assuming that'd even play in the dub, I haven't been watching that to know) would've got me jumping. Counter his Counter would've got me cheering. Because you infer so much more on something you're invested in than is necessarily there. This league was every bit as legendary as Orange Islands, to the kids watching it and seeing his Lycanrock finally get the win over Gladion's. Because we've see accumulative league efforts (each time likely getting less and less anxious to see him win because we've seen it all before) shouldn't jade the fact this was comparable to the stuff we've seen him do in the past. Hell, my favourite league battle was Gary, a league where he jobbed it next round, and even then only really the last five minutes of it when it's Charizard v Blastoise. This fight had way more significance than that. Gary and Ash barely ever fought before that match. We didn't even know Gary's team. But we hated him because he was Ash's rival. Gladion? We've seen him be ahead of Ash so often in this season. Beating him would've been as satisfying for a kid who got invested in Sun and Moon as it was for us to see Ash finally shut Gary up on the World stage.
This was as monumental as it was ever going to get. The animation was overall below par for Sun and Moon, In fact - flip the Lycanrock fight with Pikachu v Zoroark; have the two doggos double K-O, and Pikachu win out with his Z move, and it'd have been more hype from a spectacle point of view (I'm actually curious now whether that would've been received better than the Lycanrock match-up, end the tournament on a Z move), though I can still hold out hope that maybe because of the upcoming episodes we'll see where the budget went. But let's not pretend this hasn't been exactly what Pokémon battles - especially clutch battles for Ash - haven't always been like in the leagues.