I still don't get why Pikachu losing to Excadrill is such a huge deal. Iris winning the Club Battle and Ash being runner-up was fine by me, especially as we had recently learned Iris and Excadrill's backstory, which established how powerful a team they were capable of being, and Axew had his first real victory in the same tournament.
As for the Clubsplosion, he was using Scraggy, his baby pokemon who still has a way to go even now. He deliberately challenged himself and with Ash's help Scraggy beat two evolved pokemon and picked up a difficult new attack. All that said, Stephan and Montgomery were undeniably more adept trainers for that sort of tournament and had much stronger and more experienced, not to mention much larger, fighting-types. Ash did just fine and grew from the tournament. That's more important than winning the whole thing when Stephan was the more deserving character for that particular arc.
And then there's the Junior Cup. We're yet to learn how Ash loses to Trip in the finals, but while Trip is a new trainer he's a gifted one who has studied hard and is highly determined. Trip has had some disappointments in the previous tournaments and is now stepping up his game to show Ash must do the same.
Seriously, are surprises of no interest to you people? Ash can't win every time, and they've hardly come up with bad excuses to have him lose. If he lost against Burgundy with a type advantage, THEN you can complain.