What is the chronological order of the Winningverse stories? I've never read any of the winningverse stories (le gasp) but I have read My Little Denarians, Dresden Gets Schooled, and Dresden Rocks, so I know that Chengar Qordath is a very talented writer. I figured I might at least try it out.

Lets see ... I know these aren't all of the stories in the Winningverse, but here we go:

Training Partners
Cadance's Lovely Misadventure
Princesses Over Queensmoth
The Incredibly Apologetic Letters of Rainbow Dash (roughly, this story could potentially go anywhere between here and just after Training Partners)
The Incredibly Blitzed Night of Rainbow Dash
The Incredibly Distracting Flank of Fluttershy
What's In a Name
The Incredibly Thrilling Investigation of Storm Kicker
The Incredibly Infuriating Co-Worker of Blossomforth
The Incredibly Dense Mind of Rainbow Dash
The Incredibly Cool Godmother of Dinky Doo
The Symphony of a Winning Lyrist
The Incredibly Trying performance of Octavia
The Life and Times of a Winning Pony
The Study of a Winning Pony
The Incredibly Tough Mind of Rainbow Dash
The Incredibly Embarrassing Parents of Rainbow Dash
The Entirely Platonic Non-Courtship of a Winning Duo
The Incredibly Torn Mind of a Winning Daughter
The Incredibly Convoluted Relationship of Pinkie Pie and Rainbow Dash
Profoundly Peripheral Protector
The Princess and the Prankster Pets
To Serve and Protect
The New Life and Times
The Umbral Shard
Flurrygedon

5992494 5992498
Keep in mind that Chen hasn't written all of these... it's more like 3/5 or 3/4

5992494
There is the timeline thread, but the image is showing up to small for me to read any more.

5992494
tl;dr Just start with Life and Times of a Winning Pony, the core story for everything Winningverse.

As far as Primary stories go (i.e. excluding non essential oneshot/sidestories because there are too many to count)... I'd say:

Main Winningverse stories with Cloud Kicker
Incredibly Dense Mind of Rainbow Dash
Life and Times of a Winning Pony & Study of a Winning Pony (in parallel)
Princess Twilight's Profoundly Peripheral Protector
To Serve and Protect
New Life of a Winning Pony

These are a good place to get started (and give the core story) and to give better context to most of the other sidestories Dorath listed. Though a lot of the sidestories there can kinda work as standalone; it only builds upon the expanded universe (i.e. laws of magic, the magus order, the Kicker clan, etc.)
I included the two protector stories cause that sets up New Life.

The other Winningverse story that you should check out is Sunset Shimmer's Freeport Ventures. In chronological order:
A Moment in the Sun
The Freeport Venture & Freeport Sulidae
More Equal than Others
Auction Night
The Hunted
Something Sweet and Sour
A Thousand Masks
Trust Issues (follows up Auction Night)
Blood and Iron (follows up More Equal than Others)
Shimmer Mare's Birthday!!!
Blood Debts (follows up A Thousand Masks)

Besides the first two, most of the other can kinda work as standalone, with a few exceptions (being followup stories), and not all of it essential. I'm not sure if they plan on having another major story like Freeport Venture again or if it's only going to be a collection of oneshots. So to really follow the story there, you can only go through all the oneshots at the moment.
It is very important to note that Sunset Shimmer will not be going to EQG.

5992494
In addition to everything 5992611 listed, I feel like I should add The Lunar Rebellion and its sequel (by a different author) Midnight's Shadow. Both stories do some very interesting world building of the period just after Nightmare Moon's banishment, and their events are mentioned throughout Winning Pony. I would personally describe Lunar Rebellion as Chengar's magnum opus. Just bear in mind, all the characters here talk like Luna did in Luna Eclipsed, so it may be difficult at first to get into it, but once you've figured out the nuances of the language it really adds a lot to the experience.

5992494
And for the hell of it, here are the side stories, spin-offs and others. Like they said, some of these aren't necessary to follow the exploits of Cloud and company, but they put a wider scope upon the mythology and are hella fun reads.

The Great Snowball War
Shining Armor Finds His Muse
The Incredibly Dexterous Hands of a Musical Mare (nsfw!)
The Incredibly Grumpy Life of a Weather Pony
Anything But the Gala (spans a few years, but iirc starts before the OG gala episode)
Winning in Los Pegasus
The Incredibly Valuable Contract of a Sellsword Changeling
The Lesson Plans of a Winning Teacher* ("Lesson Plans" thru "Timekeeper" all parallel)
The Jamboree of a Winning Party Pony*
The Fabulosity of a Winning Fashionista*
The Temporal Manipulations of a Victorious Timekeeper** (follow-up to "Los Pegasus)
The Musings of a Winning Guardpony
The Incredibly Lonely Morning of Blossomforth
The Life and Missions of a Winning Agent*
Twilight Sparkle vs the Haunted Mailbox
Forward
In the Service of the Princess
*hiatus/cancelled **ongoing

5992967
oh my god, an entire story in shakespearean english? welp, that's going on my list.

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5992562
thanks all of you, i'll get to reading!
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