Just wanted to bring up, that part of the reason Ash used Chikorita in the Falkner battle (and there is something similar, but not the same in the Bugsy battle) is they themselves talked about overcoming type disadvantage with their given type (Falkner flying overcoming Electric types, and...
No, it's not even offscreen for either, Sobble battled the sand snake in it's debut episode, he battled Flygon, and he battled...whatever in 54, and the Grookey stuff was "onscreen" too, but unlike the Sobble stuff (in my view) Grookey one could say hasn't "officially" battled anything yet.
So, depending on what one views as "authentic" Pokemon battling, Sobble has battled other Pokemon (if you mean other Trainers' specifically, that I can't remember, but Sobble may still have). Grookey did attempt battle with Absol too (and as I was reminded, he kind of had a "sword exchange"...
Some episodes were really good for me (1, Nessa/Olive episodes) some didn't quite do that (Hop, Alister, 7). Bea was good as well, but not to the level of Nessa/Olive for me.
I don't know how much they'd know actually, because when Infernape battles Moltres, this will be the first time since BW and Charizard that Ash will battle using a Pokemon not of his current team (though given the premise of PM 2019, I don't know how relevant "current" teams needs to be). So...
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