At some undetermined time, Drake became the champion of the Orange League and was recognized as the strongest Trainer in the Orange Archipelago. His partner is a Dragonite, which is easily his strongest Pokémon, as it managed to defeat three of Ash's Pokémon in a row.
In his debut appearance in Hello, Pummelo!, Drake wondered when he would finally meet a challenger capable of defeating him. During his time as leader of the Orange Crew, Drake remained undefeated no matter how many challengers tried to beat his team of powerful Pokémon.
After easily foiling Team Rocket's attempt to steal Dragonite, Drake accepted Ash's challenge for the Winner's Trophy. Battling in a stadium overlooked by a statue of Dragonite, Drake's first four Pokémon fainted while only managing to defeat Lapras. In Enter the Dragonite, when Ash had four Pokémon remaining, Drake called upon Dragonite to battle Charizard, Squirtle, Tauros, and Pikachu in turn, finally succumbing to Pikachu's Thunder attack. Drake was extremely impressed with Ash and his Pokémon and presented Ash with the Winner's Trophy as proof of his victory.
Although the dub implies that Drake is merely a fifth Gym Leader in the Orange League, the Japanese version specifically uses the title Head Leader to denote his importance. Additionally, Drake is not necessarily a Pokémon League Champion either, given that it is not clarified whether or not he ever actually had to defeat a previous Head Leader in order to take the title (though it is suggested). In The Electric Tale of Pikachu manga, he is referred to as the Orange Crew Supreme Gym Leader. Ash battles him in Surf's Up, Pikachu.
In both the anime and manga, Ash was the first person to defeat Drake in Orange League history. Many Trainers never even got past Drake's first Pokémon, Ditto, apparently losing their cool seeing a copycat defeat their own Pokémon. Before Ash's challenge, Drake seemed bored and wondered if anyone would ever defeat him. He keeps his prized Dragonite's Poké Ball around his neck. Though no one prior to Ash had ever knocked out four of his Pokémon in a row, it is implied that some Trainers did get past his five other Pokémon only to be defeated by Dragonite, as the announcer says that he has saved Dragonite for last many times before.
This listing is of Drake's known Pokémon in the anime:
Ditto was Drake's first Pokémon used against Ash. With its Transform, it was able to completely mimic Pikachu and match all of its attacks. However, in the end Pikachu was able to outpace Ditto due to Ditto's physical condition remaining the same despite its transformation. It was defeated after Pikachu managed to stand up and knock Ditto to the ground with its tail after a prolonged race using Agility. It reappeared in a flashback in Enter The Dragonite.
Onix was Ash's second opponent. Squirtle started the battle with a Water Gun, but Onix dodged it using Dig. Ash then decided to send Squirtle into the water only to be stopped a couple feet shy by Onix emerging from underground which knocked Squirtle into the air before using Bind. Squirtle escaped Bind by using Hydro Pump. After using a Skull Bash on the now weak Onix, Ash's Squirtle won the battle. It reappeared in flashbacks in Enter The Dragonite and The Fire-ing Squad!.
Drake's third Pokémon against Ash was Gengar. Ash initially sent out Tauros, but after a failed attempt at Fissure which allowed Gengar to counter with Confuse Ray, Ash then switched for Lapras. Lapras avoided a Hypnosis attack by diving underwater where upon surfacing both Lapras and Gengar launched their respective Ice Beam and Night Shade attacks simultaneously which resulted in a massive explosion knocking out both Pokémon.
Drake's fourth Pokémon against Ash was Venusaur. It faced off against Ash's Tauros. Tauros's Fissure didn't work due to the sand field's cushioning effect. However, after surviving Venusaur's Solar Beam, Tauros was able to defeat Venusaur with a Take Down attack.
Electabuzz was Drake's fifth Pokémon. Although Electabuzz initially defeated Bulbasaur with ease, Charizard was able to withstand a Thunder Punch and a Thunder before defeating Electabuzz with Seismic Toss.
Drake appears as Ash's final opponent in the The Electric Tale of Pikachu manga. After defeating the other Orange League Gym Leaders, Ash goes to battle Drake at Pummelo Island. The battle starts with Ash using his Pikachu and Drake with his Ditto. After a long, tough battle, Pikachu manages to defeat his clone with a well executed Swift attack.
Most of the battle is not shown and it shows Drake with only his Dragonite left while Ash still has three Pokémon. Drake sends out his Dragonite which proceeds to easily defeat Ash's Squirtle. Next, Dragonite faces Ash's Charizard and despite the fact that it is smaller than its opponent, Dragonite eventually defeats it. Lastly, Dragonite faces Ash's Pikachu and despite the clear advantage it possessed, Pikachu climbs into its mouth and shocks it from the inside, defeating it. Afterwards, Drake commends Ash for his victory.
This listing is of Drake's known Pokémon in the manga:
Dragonite is Drake's strongest Pokémon. It was the last Pokémon used against Ash in their match. Dragonite proved to be powerful, strong enough to take down two of Ash's Pokémon and severely damaging a third before finally being defeated by an Electric-type attack inside of its mouth.
Ditto was the first Pokémon Drake used against Ash. With its powerful ability to take the form of its opponent, it was a dangerous foe for Pikachu. However, a well-used strategy allowed Pikachu to defeat its doppelgänger.
Drake's Gengar unofficially used the LevitateAbility to avoid Tauros and his Fissure attack despite the concept of Abilities not being present at the time. It would then have the Ability in Generation III through VI.