Game:

Pokémon Stadium 2 (2000)

Duration: 40:41

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I have made it to Challenge Cup Master Ball, the Pokémon are at Level 75, and this one has Pokémon that have high stats, most of which are fully evolved Pokémon that have a base stat total from around 450 to 550. The teams you receive are random, like the held items, moves, and the kind of Pokémon you receive, and sometimes you can get good moves or some with low base power.
List of Pokémon that can be used in Challenge Cup Ultra Ball.
Venusaur, Charizard, Blastoise, Nidoqueen, Nidoking, Ninetales, Golduck, Primeape, Arcanine, Poliwrath, Alakazam, Machamp, Victreebel, Tentacruel, Golem, Rapidash, Dodrio, Muk, Cloyster, Gengar, Electrode, Exeggutor, Rhydon, Kangaskhan, Starmie, Scyther, Jynx, Electabuzz, Magmar, Pinsir, Tauros, Gyarados, Lapras, Vaporeon, Jolteon, Flareon, Omastar, Kabutops, Aerodactyl, Snorlax, Meganium, Typhlosion, Feraligatr, Crobat, Xatu, Ampharos, Politoed, Espeon, Umbreon, Steelix, Scizor, Heracross, Ursaring, Houndoom, Kingdra, Donphan, Porygon2, Miltank, Blissey

Here is my team that I got for Challenge Cup Ultra Ball.
Porygon2: Defense Curl, Tri Attack, Agility, Blizzard (Mint Berry)
Ampharos: Iron Tail, Double Team, Thunder, Protect (Magnet)
Poliwrath: Water Gun, Toxic, Submission, Endure (Black Belt)
Victreebel: Sweet Scent, Acid, Cut, Giga Drain (Gold Berry)
Typhlosion: Attract, Headbutt, Leer, Flame Wheel (Charcoal)
Aerodactyl: AncientPower, Double Team, Roar, Wing Attack (MysteryBerry)

I did get a solid team for this one, Porygon2 has Agility to boost its Speed, and it can use Blizzard to take on Ground-type Pokémon. Ampharos is there for the Electric-type, and while Thunder is powerful, it has a chance to miss, and it doesn't even have Rain Dance, I would have much preferred ThunderPunch as it is more accurate, but at least it is better than Zap Cannon. Poliwrath doesn't have the best, Water Gun for the Water-type move, but at least it has Submission for the Fighting-type move. Victreebel does come with Giga Drain and it has a Gold Berry to restore 30 HP when its HP is below half, Typhlosion does stand out as it does have Attract to help out against some foes, and Headbutt to decrease their chances of attacking, and last up is Aerodactyl with AncientPower, one of the best Pokémon to have in Challenge Cup Master Ball.
I will list each of the Trainers and what types they tend to specialize in.
Battle 1: Twins Jan & Jane
Types: Bug x3 / Flying x2

Battle 2: Schoolboy Oliver
Types: Steel / Ground x3 / Rock x2

Battle 3: Sailor Curt
Types: Ice x2 / Water x3

Battle 4: Swimmer♀ Darcy
Types: Fighting x2 / Normal x3

Battle 5: Officer Gerald
Types: Fire x3 / Grass x3

Battle 6: Kimono Girl Emiko
Types: Various

Battle 7: Scientist Roberto
Types: Dark, Ghost, Psychic x2

Battle 8: Gentleman Travis
Types: Various

The Trainers are the same from Challenge Cup Great Ball, but they have changed the types they specialize in, for example, Twins Jan & Jane use three Bug-type Pokémon and two Flying-type Pokémon, while Scyther is likely, the reason why Scyther appears in Challenge Cup Master Ball despite not being fully evolved is that it has the same base stat total as Scizor, Scyther has higher Speed than Scizor, they can even use Flying-types like Crobat, Dodrio, or even Charizard, while the sixth Pokémon can be any Pokémon.
Next up is Schoolboy Oliver, he takes advantage of the sandstorm with Ground, Rock, and Steel-type Pokémon, and he will always have Steelix as it is both a Steel/Ground-type, and he can have Pokémon like Aerodactyl, Donphan, or Rhydon. Next is Sailor Curt, he mostly has Water and Ice-types, like Jynx, Cloyster, and Lapras, but if he has Kingdra, that can be a tough foe as Kingdra's only weakness is Dragon, which is not a common type. Swimmer Darcy makes use of Attract, and she uses Normal and Fighting-type Pokémon, her most likely choices are Primeape, Kangaskhan, and Blissey for possible Pokémon. Officer Gerald uses the sun to his advantage in using moves like SolarBeam, and he can use Houndoom, which can learn SolarBeam, other likely choices include Victreebel, Venusaur, Meganium, Arcanine, and a few others. Kimoko Girl Emiko uses Pokémon of various types, be prepared for what she has, then next is Scientist Roberto, he will always have Gengar, and his strategy is using status moves like Double Team, his other likely Pokémon are Umbreon, Espeon, Houndoom, and a few others, and the final opponent is Gentleman Travis, and he uses Pokémon of many different types, and he is another opponent to prepare for.

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