>>530520909
For this anon >>530494795

These are technically different Universes, but they are very closely related because they all use the same real life stories of Japanese Horse Racing as a base to create the plot. (So you will get A LOT of similarities between them)

This is my recommendation for a Watch Order;

UMA MUSUME ANIME SERIES;

Uma Musume: Pretty Derby Gacha Game. (Multiple Original Stories that are not in the anime) Because the Gacha is very successful new stories get added every couple of months.

Uma Musume: Pretty Derby Season 1 - TV Anime (13 episodes)

Uma Musume: 2BNW no Chikai (3 OVA episodes)

Uma Musume: Umayuru - Web Short Anime (24 eps) Casual chibi comedy. (No strict time-line can watch anytime after Season 1)

Uma Musume: Pretty Derby Season 2 - TV Anime (13 episodes)

Uma Musume: Umayon - TV Short Anime (12 episode) 4-panel gag-style anime with characters from Seasons 1 & 2. (Great for a break)

Uma Musume - Anniversary Special Animation Web short (~10 minutes)

Uma Musume: Pretty Derby Season 3 - TV Anime (13 episodes)

Uma Musume: ROAD TO THE TOP - Movie version (A compilation of 4 ONA episodes, with new scenes)

Uma Musume: A New Era Begins - Movie

Uma Musume: Cinderella Gray - TV Anime (24 - 27 episodes ongoing anime) Adaption of a Manga in the Uma Musume Universe (This Season will not adapt the whole Manga - Maybe a Second/Third Season?)