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(3 edits)

im having a brain blast now im surprised about some of the pairings being wrong but im giving it a second shot now that i did a little more research 

Winona - Deoxys (Winona being the sky obsessed person she is may have seen Deoxys meteor) (I am still surprised shes not Rayquaza, Rayquaza is on one of her teams in B2/W2 but I can't read minds or control you so write what you think works)

Liza - Jirachi (process of elimination, it hard to figure out Jirachi because there is no location to find them in game so frankly they could go to anyone) (curious what your plan is with that fact btw) 

Pheobe - Rayquaza (She trained at mt pyre, where the red and blue orbs are located so she would know about the legends most likely and be curious to meet Rayquaza)

May - Eon Duo (I dug deeper because I dont have super deep pokemon knowledge and Norman who can be Mays dad gives you the Eon Ticket to go the southern island so I think thats the connection here)  

Honestly, you're putting WAY more thought into these pairings than I did

You got Liza and Jirachi right this time, I might as well fill in the last few becasue this comment chain is getting too long

May - Rayquaza
Pheobe - Deoxys
Winona - Eon Duo