If you're looking for anime similar to Fate/Tiger Colosseum Upper, you might like these titles.
Welcome to the Tegami Bachi Gakuen, a place where all prospective Letter Bees come to learn. Taking the lectures is Dr. Thunderland and his students give him the utmost respect and hang on his every word... at least that’s what he’d LIKE to believe. In truth his small class seems more content to slack off, munch on snacks or even doze than listen to the aged professor discussing the finer points of a Bee’s duties. Nonetheless, Dr. Thunderland strives to educate those that will listen on myriad subjects, such as what spirit amber is or how to defeat a gaichuu.
Masquerading as the "mysterious" magician Mr. Rebokku, Reborn has decided to conduct group interviews using a flashing roulette wheel to select the candidates, and the quirks are far from over. With each question based on a theme, if the guests’ responses are deemed too boring by their host, then they are doomed to a merciless fate. With Reborn using his powers to force unwilling participants to answer according to his ideals and their survival at stake, just who will emerge victorious from Mr. Rebokku’s "interviews"?
Protagonist Eiji assembles "cunninglasses" so he can read his classmate's note about the boy she likes.