The Winningverse seems to have been designed to integrate very smoothly into canon, covering topics that the show avoids while taking advantage of the show's disdain for worldbuilding and backstory to fill in those aspects on its own. I can't think of anything in the show so far that has completely torn the Winningverse to shreds.

However, that doesn't mean that there haven't been minor things. After seeing Sparkler's surprisingly precocious reputation as an organizer and the undisguised Free Mind at the ceremony (Cranky has travelled a lot, but getting one, even a friend, to drop their disguise seems unlikely), I'm wondering how much has happened in the show that can't be justified in the Winningverse. Did Griffonstone break anything?

I would provide a screen shot if I could find it again but I saw a twitter post earlier from someone on the show staff that indicated the Changling was Matilda's friend and not Cranky's.

Considering everything in season 5 is more or less further into the future relative to where the Winningverse is, it doesn't seem like its much of a problem.

The only thing that really would be in conflict is possibly Griffonstone, but that could be written off as Griffonstone being only one nation, or alternatively Griffonstone is less than 900 years old.

4467001 About the only thing that got jossed was the Nightmare Rebellion.

In Winningverse canon it was a massive war. In the show it lasts maybe 5 minutes.

4467001

I'd say that the Lunar Rebellion part of the Winningverse breaks canon, but that doesn't make it any less enjoyable to read. Plus it happened during the years of Luna's exile anyway, which are open for interpretation.

Sparkler's age in general is a headcanon issue that has been shoehorned into Derpy (Muffins?) headcanon ever since Sisterhooves Social aired. It is possible, yet unlikely that she "used to be" a VIP in Ponyville in the Winningverse before Twilight came along, especially with Winningverse canon recently revealing who her biological parents really are.

I have to re-wath the episode, but I don't think anything Derpy, Time Turner, Lyra, or Bon Bon did disrupted canon much. Bon Bon could even be handwaved away as she and Lyra doing some sort of kinky roleplaying if someone's that desperate.

The changeling could have been Puzzle Piece from Freeport... stranger things have happened, although Puzzle is probably too smart to drop his disguise. It seems like that changeling would either have to be stupid or have the changeling equivalent of balls of steel to go "naked" at such an event.

4467001
I think that at the end of the day, with as many adult-themes the Winningverse throws into this setting, one has to simply accept, as with pretty much any fanfiction, that it's not going to fully integrate every aspect of the show in some respects (especially for any universe as expanded as this one). That doesn't make it less enjoyable for me, heck, I of all people should know about breaking canon when I'm writing a reimagined crossover of all things. What matters to me more than each character exactly being written as their canon versions is simply believing as I'm reading through any fanfiction (unless it's some nonsensical comedy or random fic) that these characters and events can still happen in this setting, even if they're different in style or execution from what we get in the show. To this day, the Winningverse remains something that I can totally buy as being a plausible version of Equestria, and that's all that really matters to me.

I actually haven't read the Lunar Rebellion stuff, so I can't make any judgments there myself. Did the history of the Wonderbolts break anything from that part of the timeline?

There's also the time compression issues, with the first episode of Season 1 and the first episode of Season 2 taking place exactly a year apart, which is reinforced by the Discord episode's Gala being the second one shown. How has the Winningverse handled that?

I know the Winningverse crossed my mind when Sparkler came up (did they actually call her that? I've honestly forgotten) but it's like
4467166 said, you're not gonna be able to predict the future of an ongoing series so just try and fit it in the best you can with what you've already seen. Plausibility is a greater virtue than stickler for complete canonicity that sacrifices story or character for it.

In general, a retrofitting would be nice. Conformity to canon isn't a bad thing in this case, and I would highly advise for it to be done.

4467234 The WV has established the time between the beginning of the show to mid-late Season 4 being about four years, the latter explicitly mentioned by Twilight in one of Storm's stories. If I did the math correctly correlating the show's (and books') events with WV canon...

Season 1 (Summer 1000 - Fall 1001)
Season 2 (Fall 1001 - Spring 1002)
Season 3 (Spring 1002 - Fall 1002)
Season 4 (Summer 1003 - Fall 1004)
Season 5 (Fall 1004 - ???)

I agree that the WV has meshed well with show canon with a few bumps. Surprisingly, "Slice of Life" did little to generate conflict in continuity, with the exception of Bon's secret life, but then again only Lyra's point of view has been explored in the WV.

As for the Wonderbolt issue, aye, it was addressed in Lunar Rebellion. Rising Shadows, chapter 2, if I'm not mistaken. Kudos to Chen for finding a way around that. Hell, kudos to him for kick-starting an amazing world to read and write. The guy and the rest of the gang inspired me to get writing again (even though I haven't written much )

4467279
Yeah, when it comes to Bon Bon's secret life, the only potential issue I see is how long she's been retired from monster-hunting-dom and living in Ponyville. Which, given how the show doesn't have much of a clear timeline, isn't likely to become a clear issue.

That said, these days I care more about keeping the Winningverse internally consistent than I do about matching every single little detail of canon, especially since canon remains an ever-changing thing due to new episodes coming out.

4467121 He was clearly invited so I've been head-canoning that he, Cranky and Steven had a Three Amigos dynamic going as they adventured all across Equestria looking for Matilda.

Thus why he was 'naked': He knew Cranky and Steven would back him up if anyone started trouble.

4467035

Also Sparkler is listed as Amethyst Star

4467121 What story is it that Sparklers parent were found?

4467001 Frankly, there have always been issues. The biggest one is the changeling hive mind which is very clearly disproved by the way the changelings behave in their debut, and the other very clear example is that Rainbow was shown to have a black belt in some martial art back in season 1 so the description of her as an unskilled brawler is totally at odds with canon.

4468606 Well, it isn't exactly revealed just yet, but certain clues in The Study of a Winning Pony do point to Ammy's true origins.

4469939
It hasn't been confirmed yet, but it seems to be very likely that (SPOILERS FOR The Study of a Winning Pony): Twilight's half-sister Amethyst is actually Sparkler, especially since it was revealed that she was also sent to an orphanage shortly after she was born. It would also provide an explanation for Sparkler's above average magic power. What makes it even more obvious is that Sparkler's canon name is Amethyst Star. I wouldn't say that her appearance in Slice of Life completely contradicts this theory, since it interestingly enough even further confirms it. By sheer coincidence, Amethyst and Twilight both having a talent for organizing speaks in favor of them being half-sisters. It may seem a bit far-fetched, but it still strongly implies that they're both related in the Winningverse, especially with all the evidence we already have. I have faith in the Winningverse writers that they may even turn the recent canon revelations to their advantage if they do it well.

4467073
Actually, The Lunar Rebellion takes place over a century after Celestia banishes Nightmare Moon, so there is no conflict there.
I do agree that, the fight between Celestia and Nightmare Moon is disappointingly short, and it definitely contradicts the several fanfics written before Season 4.
But thankfully, not the winningverse

The show hasn't really covered much about the centuries during Nightmare Moon's banishment, which is great for fanfics.
It's all
: "Over/ Around/ Less than one thousand years ago."

Rainbow Dash's Proclamation that she has two mum's. With Radical Mum and Awesome Mum.
Would probably need to be retconned to be Aunts.
That's one of those smaller details that would need changing to bring it into line with the main series.

Parental Glideance

Seasoon 7
https://youtu.be/aGjA6RTVQ3s