Hey there! The item description of Medlar Fruit actually mentions a scenario similar to this!

"This item will raise your lion's training bar by 5% per fruit used. It's useful if your lion is close to filling out their training bar and they're aging up soon! If used on a lion that was not cub trained, very little bonus stats will be granted."

From what I can tell, this implies that Medlar Fruit is just a flat 5% boost regardless of age, and that Cub Training from Crossroads is a special event when it comes to the general training bar where the bonuses of it can only be obtained by Cub Training in Crossroads and nowhere else. I hope this explanation makes sense!

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