While many Pokémon fans wished for Ash to evolve his Pikachu at some point in the series, there are several other Pokémon that would have benefited from evolution more than Pikachu, with the top contender being Gible, a late addition to Ash's Sinnoh team.
Ash has a tendency to let his Pokémon decide for themselves whether they want to evolve. Unfortunately, this approach has resulted in many of his Pokémon, including Pikachu, remaining in their basic forms and not evolving. As a result, Ash often finds himself at a disadvantage in competitions as he is one of the few trainers who use unevolved Pokémon. This disadvantage became particularly apparent during the Sinnoh League's Lily of the Valley Conference. In this tournament, Ash faced off against opponents with fully evolved Pokémon while battling with his newly caught Gible, which he had only obtained around thirty episodes prior to the tournament. Despite Gible's impressive performance in the battles leading up to this point, it was swiftly defeated when Ash went up against one of his most formidable opponents, Tobias.
Ash's Gible's Evolution Could've Won Him the Sinnoh League
Ash often takes a considerable amount of time to evolve his Pokémon. Acquiring Gible just thirty episodes before the tournament put him at a disadvantage in terms of evolution. Most of that time was spent helping Gible master its Draco Meteor attack, which inexplicably always seemed to hit Dawn's unfortunate Piplup instead of its intended target. Unlike Pikachu, Gible didn't resist the idea of evolving and even seemed interested in doing so. If Ash had more time with Gible, he could have entered the tournament with a powerful Garchomp, one of the strongest Pokémon at that time. This would have had a significant impact on his overall success.
Garchomp is classified as a "pseudo-legendary" Pokémon, a type that is nearly as strong as legendary Pokémon when fully evolved and typically quite rare. The challenge, particularly in the anime, is obtaining a Gible in the first place. If Ash and Gible had trained diligently and evolved it, having Garchomp in the tournament would have given Ash a much stronger position. Garchomp would have been able to put up a significantly tougher fight against Tobias' Darkrai, for instance. It is particularly noticeable that, among Ash's Dragon-type Pokémon, Gible is the only one that didn't achieve its full evolution, unlike Goodra, Noivern, and Dragonite, by the end of the series.
Having given Ash a fully-evolved Garchomp would have brought an intriguing dynamic to his eventual showdown with Cynthia in the Masters' Eight tournament, as she also possesses a Garchomp as her most powerful Pokémon. Witnessing a clash between two formidable Garchomps would have undoubtedly presented an intense battle, especially considering the frequent switching strategies employed during their match. Additionally, Garchomp's ability to undergo Mega Evolution would have added a further layer of uncertainty, leaving fans wondering about Ash's secret weapon. Unfortunately, Gible never had the opportunity to evolve, primarily due to its late capture in the series. Thus, viewers were deprived of the excitement of witnessing Ash engaging in battle with a beloved Pokémon like Garchomp.