(Takes place within the universe of "The Sitter with the Diamond Tiara" and its semi-sequel "A Dazzling School Daze".) Plagued by uncertainty about her future, Diamond Tiara visits Cheerilee in hopes the teacher can guide her one last time.
For four years, Sunset Shimmer has carried a torch for Miss Cheerilee, and for four years, she's struggled to look at her without thinking of the one who got away.
When Sunset Shimmer gets a letter from a not-so-secret admirer, she thinks it's just a bump in the road. She doesn't know it's all about to end. But Cheerilee knows. She's always known.
After Anon's arrival in Equestria, it was decided that Ms. Cheerilee would act as his guide and teacher while he gets adjusted to his new life. Neither of them are happy about it.
Sunset deals with the effects of the Fall Formal while Cheerilee learns how hard being a parent can be. Together, the mother and daughter learn more about each other and deal with more challenges.
When leaving the school after a long day of teaching and doing paperwork, Cheerilee catches a student sleeping outside in a bush and takes her home. It goes further than either of them thought. Follow this adventure.
A new bully strikes fear into everypony at Ponyville Schoolhouse, and her name is Dinky Doo! She's the baddest of the bad, and it falls to Cheerilee to set the filly straight before it's too late, at least according to Dinky herself.
The fifteenth installment of What If series that involves the rewriting of episodes. Ten episodes from Seasons 1-3, and 6-8 are included this time, including redos, and a reworking of an episode. (Warning!: Rewrites based on personal opinion.)
(An unofficial continuation of Tailslover13's "Total Magic Pony Island", takes place in AU after "The Return of Harmony".) The long forgotten missing episodes of Total Magic Pony Island are here. Find out which contestant will win it all!
(Rated Teen to be safe.) Cheerilee decides to turn herself into a foal, so her students will have hoofs on experience taking care of one. But are her students up to the task of caring for their foalified teacher?
After an unfortunate accident, Spoiled Rich wakes up thinking she's her old self before her marriage to Filthy, and boy isn't she different. The whole town is shaken up in the process, and Diamond is about to uncover some long lost family secrets...
An alternate take on events during Hearts And Hooves Day, where after they drink the Crusaders' love potion, Cheerilee and Big Mac take things just a little too far.
It's Family Appreciation Day once again, and Scootaloo's aunts/parents are making their long awaited debut. Unfortunately, their arrival coincides with Filthy and Spoiled Rich's presentation and, well...