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If you haven't met certain criteria for this, such as obtaining their phone numbers or visiting the Fighting Dojo at all, you won't have that courtesy. Once you have the Leader's phone numbers, you can call them and challenge them any time you want, and they will wait for you in the Fighting Dojo at certain times.

To get their numbers, you need to talk to them at certain places at certain times. Here's a list (If no timing is listed, then any time on that day):

Falkner: Celadon Department Store on Monday. Rematch time: Saturday morning

Bugsy: Either Ilex or Viridian Forests on Thursday. Rematch Time: Thursday afternoon

Whitney: Goldenrod Dempartment Store on Saturday, 12 PM til 4 PM. Rematch time: Saturday Afternoon

Morty: Bell Tower on Mon or Tues. Rematch: Tuesday night

Chuck: Get # from his wife. Rematch: Wedsday night.

Jasmine: Olivine Diner any day between 1 PM and 2 PM. Rematch: Wedsday afternoon

Pryce: Lake of Rage on Saturday, from 6 AM til 10 AM. Rematch: Monday morning

Clair: Dragon Den everyday from 6 AM til 10 AM. Rematch: Friday evening.

Kanto Leaders

Brock: Diglett Cave everyday from 12 PM til 3 PM. Rematch: Saturday evening

Misty: Route 25 everyday from 4 PM til 6 PM. Rematch: Wednesday morning

Lt. Surge: Have Pikachu first in your party at the Power Plant after defeating Zapdos, everyday, from 9 AM til 11 AM. Rematch: Friday morning.

Erika: Fountain in Celadon City on weekends from 3 PM til 5 PM. Rematch: Sunday morning

Sabrina: Olivine Harbor on Friday. Rematch: Sunday Afternoon.

Janine: Poke-League Reception Gate everyday from 4 PM til 6 PM

Blaine: Cinnibar Island on Tuesday. Rematch: Tuesday afternoon.

Blue: Now, Daisy will massage your Pokemon to make them happier. Once you receive seven of her massages, she'll give you Blue's number. Rematch: Sunday Night.

Hope I helped!

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