Rarity is alone on Hearts and Hooves Day, and she's not happy about it. A friendly afternoon in the park with Applejack promises to turn their friendship to something more – or at least it would, if either of them would simply talk to the other about it.

Between her awkward sort-of romance with Applejack, her desire to help Fluttershy find a special somepony of her very own, family, friends, and the general day-to-day chaos that is life in Ponyville, this fashionista's got her hooves full.

Side story to The Life and Times of a Winning Pony and the rest of the Winningverse. My thanks to Chengar Qordath and Comma-Kazie for their support and pre-reading assistance.

Perhaps Doctor Whooves is not a medical doctor or a time lord, but a doctor of psychology.

The following are his journals after he receives instructions from Princess Celestia to permanently set up shop in Ponyville to keep an eye on Twilight Sparkle and her friends, where he learns more than he bargained for.

View the Google Docs table of contents: https://docs.google.com/document/d/1gCeHce9BTZ48P5fxNQDHq7diYlNqJIbkZNdMGLN3H5k/edit?pli=1

Spartans never die, they're just missing in action. This has never been more true for Jorge-052 as, after activating the slipspace drive that was supposed to kill him, he is instead flung into a strange world where war is but a distant memory. Will the aging soldier be able to adapt to this new peaceful planet? Or will his only salvation be found in finding a way back to his own chaotic universe?

(It's my first time, so be gentle)
Now featuring a TVTropes page by Sabo88

This story is a sequel to Ascend

Congratulations, Twilight. With Celestia and Luna on their constitutionally mandated vacation, you're in charge of Equestria. The position of Regent is an honored and hallowed one. But maybe it's a bit early to congratulate you. After all, whether it's a nobility jealous of your ascension, or a military unhappy with Celestia's decisions; one thing's certain: your reign will be anything but peaceful.

WANTED:

The newly crowned Princess Twilight Sparkle has set up a bold new initiative to discover new magic, and is sending out an open call to the unicorns of Equestria to apply for her research team. No experience in magical theory or research necessary. Enthusiasm and out-of-the-box thinking a must. The Equestrian government is not responsible for any physical, emotional, or magical trauma experienced during the course of the project or the application process.

Cover art by Page Turner

This story is a sequel to My Little Caboose: Blue is Magic!

It has been one month since the Elements of Harmony were used to trap Discord again, and it has been one month since Twilight lost one of her closest friends, the only consolation of which being that Church was finally getting some well deserved rest. At least, that is what she and the others believed. Discord, still trapped within Church's mind, has been picking away at his sanity the entire time, messing with his memories, making him forget what was real and forcing him to remember what wasn't. When he finally escapes, will Church be able to distinguish between reality and the memories Discord tampered with, or will his slim grip on reality finally give out?

If the ponies he is led to believe are his friends are of any indication, probably the latter.

[Before asking questions in the comments, please read!]
- This is a sequel to the completely unjustifiably popular, My Little Caboose: Blue is Magic!
- You probably will be extremely confused if you have not read that before this.
- You probably would be even MORE confused if you have never heard of Caboose.
- Click here to watch the series if you have not.
- FAQ

Ditzy Doo is the daughter of a prominent family in Canterlot. So why has she shown up at Rainbow Dash's doorstep, years after they last saw each other? Rainbow is willing to go to out of her way to help an old friend, but she may get more than she bargained for: being away from home isn't the only thing Ditzy has to adjust to...

A prequel to the events of both continuities in The Winningverse.

Co-authored by Chengar Qordath.

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

Cloud Kicker might just have the wildest life of any pony in Equestria. That may just be why Princess Luna wants Twilight Sparkle to study the insanity that is Cloud Kicker's life for a sociology report. Unfortunately for Twilight Sparkle, she is going to have to survive the circle of jealous friends, paramours, enemies, crazy co-workers and disappointed family members that surround this crazy pony. Will Twilight Sparkle be able to complete this assignment before it spins out of control, or will she be reduced to a neurotic mess?

A Winningverse Story.

Dearest Billy,

It is with a heavy hand that I must relay: He is dead, and passed away among his bees only some hours ago. I, too, am not long of this earth, thus it falls to you to publish my final wish. The attached parcel is my tin box--you have ferried it hither and thither before--and it is where notes from all our adventures, spanning two centuries, as many wars and three monarchs had been safely kept. The remaining bundles within, however, we agreed some time ago to never publish, lest our reputations be shredded. However, with his passing heavy on my mind, I cannot forget such cases, so singular and impressive that they prove, without a doubt, that Sherlock Holmes was the greatest detective London, Britannia, and Worlds beyond our farthest imaginations could ever have known.These cases will confuse you--perhaps even tarnish your memories of us--but mark my words: they are as true and real as the paper upon which you read this letter.

Most Faithfully,
Dr John. H. Watson MD