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Champions of Equestria

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safe2271510 applejack208269 fluttershy269529 pinkie pie266263 rainbow dash291283 rarity226146 twilight sparkle371848 g42130425 azumanga daioh105 chart1066 crossover75464 kagura10 kasuga ayumu23 mane six38981 mihama chiyo15 mizuhara koyomi10 osaka42 sakaki12 takino tomo16
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Background Pony #D02F
I should add that I connected Chiyo with Rarity through their skills/talent at cooking/designing.
TenaxViator

I don’t really like this kind of thing. You can never connect the characters succesfully. Hell even the two traits of each pony are debatable.  
Another good example would be “the five man band”. It’s impossible.Each of them matches several options. Those characters aren’t that simple.
deactivated5398f3

That’s the problem with trying to connect 2 ponies to each person. Some of them aren’t like 2. Some are like 3-4.
 
It’s like all those people that tried to do direct Avengers comparisons and no one ever agreed who would be who because it’s nearly impossible to perfectly match up character traits.