 If you liked
Glass no Kamen (2005)
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 ...then you might like
Haikara-san ga Tooru Movie 1: Benio, Hana no 17-sai
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A stubbornly plucky heroine who is a borderline tomoboy, of "average" looks, but otherwise impressively talented? Check. Be ready for those melodramatic shoujo plot twists, and for all the male leads to be somehow inclined to help/be in love with our single-minded girl.
If you felt Haikara-san was too short and fast paced, treat yourself to Glass Mask.
both glass mask and haikara-san are a remake of older anime, adapted with more beautiful animation, but staying true to the touching writing of the original manga.
both are romantic stories that follow an independent feisty girl who just can't get that one annoying guy out of her head, even though she doesn't like him (sure you don't, girl)
from episode 25 in glass mask, it shows a story called 'heavenly light'. this story in particular shows a lot of aspects that are similar to haikara-san, it both being about young women with strong personalities during the taishou period.