In fairness to Ash, he did brought with him only the fully evolved ones with Pikachu for the 3-on-3 Finals...
Lycanroc in fact seems quite fitting given Matsumoto's love for dogs.
Even in the anime, type effectiveness doesn't affect Counter. It just deals double damage back.My only problem with the dog battle is Dusk tanked too many super-effective Counters. It managed to handle the Stone Edges and even Outrage, but the sheer number of Counters made it feel unrealistically tanky, as if clad in plot armour.
Simply having Lycanroc stop attacking to avoid the Counter would have made it easier to accept. It did that once, but kept attacking into Counters two more times after that.
Pikachu did win the Orange League. So, it's only game-canon Leagues he's lost.Dusk (and Pikachu) are underrated. So many people, myself included, were fearful Dusk would fail like Charizard and Greninja did before him. It's great that he came through in the clutch.
And we forget that Pikachu hasn't won a Pokemon League either, despite participating in every single one and getting KO'd in almost every match. He's as much a Champion as Ash, and he deserves all the accolades.