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Brock
Pewter city
Geodude: Level 12 ( Rock-Ground )
Onix: Level 14 ( Rock-Ground )
Use Bulbasaur or Squirtle, Because Charmander's fire based powers do diddly squat against both rock and ground types. If you started out with Charmander, level up Pikachu to at least 16. You do this because Thundershock has no effect on both so you use Quick Attack. Have a Charmeleon & use embers, not Scratchs. You get a TM 34, which contains Bide.

Misty
Cerulean City
Staryu: Level 18 ( Water )
Starmie: Level 21 ( Water-Psychic )
Use either Bulbasaur ( which should have evolved into Ivysaur by now )or Pikachu ( at least level 18 ). Both Squirtle and Charmander do poorly against her water Pokemon. You get a TM 11, which is Bubblebeam.

LT. Surge
Virmillion City ( Need cut ability to get past bush )
Pikachu: Level 18 ( Electric )
Voltorb: Level 21 ( Electric )
Raichu: Level 24 ( Electric )
Best chance is a Ground type Pokemon, I would advise capturing a sandshrew from route 4 ( area after MT. Moon ), because you'll be able to train it more, and make it powerful enough to defeat all three! A Geodude would do even better because it's rock abilities prevent it from getting delt almost any damage from normal attacks. You get a TM 24, which contains Thunderbolt.

Erika
Celadon City
Victreebell: Level 29
Vileplume: Level 29
Tangela: Level 24
Best chance against Erika are either Fire, Ice, Poison, Flying, or a Bug Type Pokemon. You get a TM 21, which is Mega Drain.

Sabrina
Saffron City
Alakazam: Level 43
Kadabra: Level 38
Venomoth: Level 38
Mr. Mime: Level 37
Best chance against Sabrina's Pokemon are Bug, Ghost( for the Psychic pokemon) & Ground or Pyschic ( For the Bug-Poison Venomoth ). You get a TM 46, which contains Psywave.

Koga
Fuchsia City
Koffing: L37
Muk: L39
Koffing: L37
Weezing: L43
Best chance against Koga's poison pokemon is a Psychic, Ground, or Rock-Ground pokemon. You get a TM 06, which is toxic!Blaine
Cinnibar Island
Growlithe: L42
Ponyta: L40
Rapidash: L42
Arcinine: L47
Best chance would be using water,ground, or rock pokemon & attacks. You get a TM 38, Which is Fire Blast.

Giovanni
Viridian City
Rhyhorn: L45
Dugtrio: L42
Nidoqueen: L43
Nidoking: L45
Rhydon: L50
Best chance would be to used grass, water, & flying pokemon. You get a TM 27, which contains Fissure.

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NY
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America


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