I found out that Skyla has this pretty obscure bit of dialogue (it only plays if the player loses against her in the PWT) where she talks about knowing Winona and wanting to face her in a battle. And since Winona is visiting to participate in the tournament, I imagine there were able to!
This got me thinking… Winona and Skyla is a pretty nice relationship isn’t it? Besides this small interaction from the main games, they’re actually good friends in Pokemon Masters!
Skyla points out their similarities but I also think Winona might remind Skyla a bit of Elesa- while she seems very graceful and elegant, she also has a slightly lackadaisical side as well. It would make sense if Skyla is drawn to people like that, especially because, despite her type-preference and occupation, she can keep people like Winona and Elesa grounded, LOL










