• Member Since 30th Nov, 2011
  • offline last seen Sunday


I never make mistakes. I thought I'd made one once, but I was wrong.


Cheerilee loves teaching. Despite all the trials and tribulations it presents, it's worth it in the end when her students learn something new. Not even a letter from the Ministry of Education reminding her about the impending teacher evaluations can sway her. But tack on her new relationship, the constant 'help' of the Cutie Mark Crusaders, and some strange behavior from Dinky and Sparkler, and her life is about to become a lot more complicated.

This story is set in parallel with The Life and Times of a Winning Pony and The Study of a Winning Pony with the approval of Chengar Qordath, Comma-Kazie and Ponibius.

Cover art used with permission, source is here

Chapters (3)
Comments ( 160 )

Many, many heartfelt thanks go to Chengar Qordath, Comma-Kazie, and Ponibius for allowing me to make my own contribution to their shared setting. In addition, more thanks go to them and Aegis Exemplar for helping me with plot development and correcting my atrocious grammar :rainbowlaugh:

Ah, Cheerliee. So many shenanigans to suffer through, so little time for us to enjoy them.

Definitely looking forward to more.

It's off to a nice start, and I'm curious to see where things go from here. Cheerilee is always fun.

Haha, fantastically victorious. Fitting addition to the Winning Pony stories.


Nice work so far, and I am really wondering what you plan to do with this. Cheerilee does not really play much of a roll in CK's life outside the sleepover disaster, so you have a lot of freedom to work in your own direction without running into that plot or Twilight's research.

Wow... yeah I'm totally digging this story. Great job, and man I feel so sorry for Cheerilee. I know the feels she has all too well. The terrors of babysitting small children like that could be classified along side waterboard torture.dl.dropbox.com/u/31471793/FiMFiction/emoticons/misc_Cheerilee.png

Looks promising, I'm curious to see where this is going to go. Faved and thumbed up

A Pinkie Sense for the exact location of Dashie, I love it. Especially the bit with her ear.

Huh, so CheeriMac. Works for me, as much as I like some other Mac ships, this is the one that really seems most likely to eventually become canon, if any ship ever does that is.

I had totally forgotten about Cheerilee and the sleepover at the beginning of Winning Pony, hilarious to see her side of it. The Young Daring Do book is a nice touch.

The Winningverse is fast becoming my favorite alternate Ponyverse. This looks like it'll fit in nicely.

You silly, silly pony. You've created a monster, mate.

The Winningverse is awesome :pinkiehappy:

Well written, funny, good characterization, thumbed and tracked. Though I am curious how you will tie the rest of your story into the winningverse. I may just be forgetting swathes of literature, but I don't recall Cheerilee having a major role beyond this sleepover. Great job with dl.dropbox.com/u/31471793/FiMFiction/emoticons/sillyfilly_Sweetie_Belle.png dl.dropbox.com/u/31471793/FiMFiction/emoticons/sillyfilly_Scootaloo.png dl.dropbox.com/u/31471793/FiMFiction/emoticons/sillyfilly_Applebloom.png , they always proide a good laugh when handeled properly :raritystarry:

1549931 Well that's just what interested me. She didn't have a role in Cloud Kicker's interactions and misadventures, but Ponyville's a big town, and the pegasi aren't the only ponies living there. So their internal behavior is going to ripple through the town, and I wanted to try exploring that from a non-pegasus angle. Plus, Cheerilee is awesome :rainbowlaugh: and I'd always wanted to write something involving her in a leading role.

I know i usually say Cloudy gives me too much credit, but he really did this time :derpytongue2:

1549321 Thanks :twilightsmile: I'd always wanted to see more of the story that got skipped by necessity, since Cloud Kicker wasn't there for it. So, here I am :rainbowlaugh:

Also, I feel terrible and silly for it, but I keep reading the "How did this happen?" line in the Heavy's voice :facehoof:

awesome story another story from the main story I love it :twilightsmile: I wonder how this story will go for Ms Cheerilee

oh, this is awesome! Really well written so far, I'm really interested on how you'll continue! Nice! :twilightsmile:

It's always nice to get another addition to the Winningverse. :twilightsmile:

Faving now on the premise of it involving the 'Winningverse', will edit after reading :twilightsmile:

Edit: A most enjoyable read, I will be interested to see where you take this, seeing as you are tackling not only a secondary character, but one that holds very little place in the original story besides this scene. Keep up the great work, and have a cookie! :pinkiehappy:

I look forward to seeing where this story goes. It looks like it has potential, and I hope to see good things from it.

Ah the joys of a teacher, trying to avoid the Birds and Bees lecture. Just remember the rural students tend to know all about such things far in advance of the urban ones.

Oh my Celestia this was the perfect chapter! It was hilarious and made me squee at all the little tidbits: I like the idea of Sweetie and Silver being the smart girls, I love Dinky being the firefighter (like her costume!) and her hugging the fire extinguisher at the end? Heee! Love it! Ah, I sooo need to write something for Winningverse.

This was awesome! Insta-fave!!!

Well then Mr. Hammer. I believe the game for the featured box ha begun.


I guess I can read another great fic from the Winningverse while I wait for every single other one to update.

Oh dear bucking god Sweetie Belle is cooking.


The Winning-verse sure is growing. It's no Fallout: Equestria yet, but it's gaining a pretty decent spread of side-stories, considering Life and Times of a Winning Pony is itself technically a side story.

I really want to read this right now, but I have to work on my own writing at some point and maybe I should try and hunt down some kind of nourishment this week... To the Read Later list!

I'm loving Dinky as the unofficial (and highly necessary) CMC firefilly. :)

I think we can guess what her cutiemark is going to be! I'm thinking flames in one of those red circles with a line through it. She is destined to be Dinky Hooves, firemare exraordinairre!

Momma will be SO PROUD of her muffinette! :derpyderp1:

I'm in on this. I'm always up for Cheerilee.

Brilliant, absolutely brilliant. I love seeing more people add to this universe.:pinkiehappy:
Fav'd, tracking, can't wait to see more from all of you.:heart::heart:

Someone for the love of god teach sweetie how to cook :rainbowlaugh: awesome story so far

"Winning pony" is a growing thing now isn't it?

I'm a little torn. Up until Cloud Kicker shows up this is bland and boring like a blank fresco, but after “I got tricked into foalsitting the Cutie Mark Crusaders.” everything gets enormously better and more interesting. I know the first half has something to do with the main plot arc or something, but I'm positive you could've made it feel less like filler without sacrificing anything (unless Chekhov's guns everywhere, but I doubt it).

I'm gonna see what happens.

Why was I expecting to see tentacles emerging from the oven?

Oldguy Cloud takes on WV

What could possibly go wrong

Edit: Read because prints apparently liked it and he is the allmaster of Cheerilee. It was nice, lol.

Sweetie Belle's Cooking....

Good luck Cheerilee.

And then Dinky's cutie mark was a fire extinguisher! :pinkiegasp:

Brilliant, simply brilliant. :rainbowlaugh: Good to see that Sweetie Bell's uncanny ability to burn cereal remains constant. dl.dropbox.com/u/31471793/FiMFiction/Sweetie_Belle_lolface.png


These children need to be beaten black and blue. Are they that thick headed not to realize what they doing is wrong?!:fluttershbad:

2 homes destroyed! 2 very innocent ovens massacred, nay slain for simply existing!:twilightangry2:

I would of tossed their asses out the door and not look back.

Cheerilee....W'ere is my sista?
Yes, Darling, where is Sweetiebell?
I threw their crazy flanks this morning!

Well, this looks both entertaining and promising. I look forward to more of this installment of the Winningverse.

Wow, who knew the winning pony would give way to such an universe. And hey, cheerintosh! That's definitely something I wanna see :pinkiehappy:

Good, funny, start, gonna check out how it keeps going

Blossom's "swords"...
That cracked me up! (For some reason, all I could picture was Twilight running around the house with one of them yelling in Stiffler's voice, "FILLYFOOLER ARTIFACTS!!!")

“I don’ think those were swords, swords are supposed to be hard and made of metal, aren’t they? Your sister’s were all made of that weird rubbery stuff,” Applebloom said, her eyebrows narrowed in thought.

“Maybe they were training swords, what do you think, Miss Cheerilee?”


Ah its Featured. Good story too.:pinkiehappy:

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