To be updated periodically as new chapters, stories, and authors come into play.

UPDATE - December 30 2012.

Changes: Added new fics and authors.

Awesome!

UPDATE: - January 18 2013

Changes: Added The Lunar Rebellion and updated the timeframe for said story.

UPDATE: February 21, 2013

Changes: Added The Incredibly Embarrassing Parents of Rainbow Dash, The Incredibly Distracting Flank of Fluttershy, and The Incredibly Cool Godmother of Dinky Doo.

When will the collab shorts be released?

Oh, something I noticed: in Life & Times, Cloud Kicker mentions that Sparkler is 15 or 16, and in Study Of, that estimate is narrowed down to 16. Unless I'm mistaken, that should put Sparkler's age at 14 when she was adopted.

Also, any chance of getting this updated once CK Month is over? I'd find it incredibly useful for... um, things. Let's just say that piecing together a complete, definitive timeline would be a major godsend for me, hmm?

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Adding in timeline-important episodes, like the Wedding, would also be pretty huge.

UPDATE: June 4, 2013

Phew, it's been a while hasn't it? Changes: Added various stories from the Winningversary. Note: If your story hasn't been added yet, it will be once the story folders are accessible again. Current website issues prevent me from accessing all of them.

Dunno if mine's gonna show, as Cloud has only appeared once; twice without a line when the next chapter arrives. If you're interested, PM me ... just in case.
Dammit, where's the Cloud Kicker emoticon!?!

UPDATE: July 13, 2013

Added The Incredibly Torn Mind of a Winning Daughter

So while doing some research, I ran into a bit of a temporal anomaly in "The Life and Times of a Winning Pony" chapter 5 "The Pony Who is On a Drug Called Cloud Kicker."

The reason RD wishes to remain in Ponyville seems to be describing the events of S2E3 "Lesson Zero." Directly after the scene where RD delegates to CK, we have CK in Cloudsdale where she remembers events from S2E4 "Luna Eclipsed." Perhaps I am mistaken in attributing RD's words to refer to a different canon event than Lesson Zero? Or does the Winningverse use a different timeline? (the coincidence that this possible anomaly deals with Lesson Zero does not escape me). the only other explanation I can come up with would be that the events of "Luna Eclipsed" occur between scenes... which seems like a rather unusual bit of story to leave out.

Related though possibly independent to the above, Both episodes occur before S2E17 "Hearts and Hooves Day" which is supposedly when the prequal of the entire story takes place. While CK remembering events of Luna Eclipsed are fine with this timeline, it still seems odd for RD to be referring to "Lesson Zero" in the present as it were.

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Chapter five of WP doesn't have Rainbow referencing the events of "Lesson Zero" as her reason for remaining behind, but "It's About Time."

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For some reason I mixed the two episodes up.

Derp.

UPDATE: September 30, 2013

Added The Incredibly Grumpy Mind of a Weather Pony, The Incredibly Thrilling Investigation of Storm Kicker, The Incredibly Trying Performance of Octavia, The Incredibly Conflicted Mind of Pinkie Pie, Incredibly Valuable Contract of a Sellsword Changeling, and The Incredibly Lonely Morning of Blossomforth.

someone with more free time then me should add up the words for the entire winning verse be something epic lol

By chance where does Freeport Venture happen in the Winning Continuity?

4530175 Considering Cadance became an alicorn about six months prior (and was a teen at the time), I'd guess about fifteen or so years before Season 1.

Im new to the Winningverse and i need to know what the first story is!

5365019 That depends on what you mean.

The first one written was the Incredebly Dense Mind of Rainbow Dash. The one where Rainbow and Pinkie go on a Hearts and Hooves day date. After that The Life and Times of a Winning Pony.

The first one chronologically is The Lunar Rebellion.

So trying to figure out the normal timeline it seems that Tirek's attack would be late summer or early fall, depending on when the Equestria games were meant to take place. It does seem to be hard to place where episodes are season wise since it seems that the season is more plot based than anything.

Cause Tirek attacks, then the cutie map happens, and a few episodes later is the episode with Tank hibernating. So late summer, early fall. Cadance would be announcing her pregnancy maybe spring-ish. Starlight doing the timeline stuff has to happen almost a year later, because the Crystalling is her first lesson so she could only have been Twilight's student for a few weeks. Though that Heart's Warming happens not long after Crystalling suggests it's more fall/winter.

If the games were in the spring, and Tirek attacked summer, Cutie map is shortly after that. Cadance announcing she's pregnant would be winter, that would work timeline-wise. Course that would likely mean that Equestria has a year-round school schedule.

Other people thoughts? I am putting this here since it does sorta impact the Winningverse as Cloud's foal would be born half a year before Flurry. Also because it helps figure out for people writing and needing to know when to have something.

Bump?
Where does Eakin's Changing Lives fit? Apparently it happens during the second invasion, thus, after Tirek's shenanigans.
I went here to get a grip at what's happening and in which order should all thos stories be read to avoid confusion...
Well, for example, that story...
https://www.fimfiction.net/story/377132/articulate-arguments-about-augmenting-ancient-ancestral-armor
...apparently, happens after Storm fought Tirek(?) in Shadow's armor. But I couldn't find anything related to that anywhere else.
I'm lost and I need a map. I think I'm missing on some good stuff.