Continuity mistake: When the Poké Ball Ash uses for Krabby indicates success, it is at a 22° angle, and there are pieces of wood on the ground, but when Ash goes over to retrieve it, it is at a 45° angle, and the pieces of wood previously on the ground have disappeared. (00:04:49)
Continuity mistake: When Team Rocket takes off in the boat, it sinks. Their pokeballs float away, and Jessie says "Arbok and Lickitung are floating away!" But she doesn't catch Lickitung until Princess Versus Princess (Season 1, Episode 52).
Factual error: When Venonat uses Stun Spore, Ash tells Bulbasaur to use Whirlwind. Bulbasaur just blows the powder away with his mouth, but he doesn't use the Whirlwind attack. He can't learn Whirlwind in any of the games, and what Whirlwind is supposed to do is to blow the opposing Pokemon away. Ash could have just as easily told Bulbasaur to blow it away, but he instead chose to tell him to use a move that he can't possibly learn. The only Pokemon that can learn Whirlwind are either Flying types or Bug types; i.e., Pokemon with wings (with the exception of Makuhita and Hariyama, which weren't introduced until generation III, and did not exist at the time this episode aired). In The School of Hard Knocks (Season 1, Episode 9), a character mentions information regarding a Pokemon's levels, attacks, and information which is taken straight out of the game, so it's very clear that Bulbasaur should not be able to use Whirlwind. [This is a result of mistranslation. In the original, Japanese version Ash orders Bulbasaur to "blow it away." He didn't say Whirlwind. Still a mistake in the English version.]
Other mistake: The Pokemon Exeggcute is shown evolving in to an Exeggutor naturally. But the Pokemon Exeggcute can only evolve into an Exeggutor with the use of a leaf stone. In the Japanese version, there is a mention that something in these woods causes Exeggcute to evolve without using the Leaf Stone (when Exeggcute evolves, James even mentions that there is no stone). However, as this was skipped in the English version, it creates a plot hole.
Plot hole: After Ritchie tells Misty that he never talked to them through a phone, Misty could have put two and two together and realised that Ash was told to go somewhere by someone impersonating Ritchie and that he might be in serious danger. However, she does absolutely nothing to help Ash, she doesn't even inform Brock about it.