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Background Pony #47B8
@Tjxen Dlue  
I can’t think of any other moment in the show where they don’t win and it isn’t part of the plot.
 
They’re are moments where they do win. Then there are moments where they don’t win like how Applejack failed to get blue ribbons, which sets up the whole episode, or when Rainbow Dash fails the race of the pets, which sets up the moral.
 
But the thing with the race with Twilight, and the race with Rarity-Sweetie Belle; aside from it being confirmed they didn’t won, there’s nothing to it. They could have won and that changes nothing about the episode.
 
I think more kids shows should have this. The main characters shouldn’t win every competition and there shouldn’t be a big moral or plot point about it. Winning shouldn’t be the default, or expected. I think it would be healthier for kids not to expect to be the best in everything. I’m not asking for participation trophies; just that the main characters shouldn’t win everything.
Liggliluff
Best Artist - Providing quality, Derpibooru-exclusive artwork
Helpful Owl - Drew someone's OC for the 2018 Community Collab
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Artist -

@Background Pony #3582  
Disqualified for helping the opposing team? Rather disqualified for potential distraction.
 
Also; of course she got a bulls-eye. It’s either perfect, or a complete failure.
 
I liked how Twilight only got 5th place in the Running of the Leaves … or that Rarity+Sweetie didn’t win Sisterhood Social.  
…the main characters doesn’t need to be perfect.
Background Pony #9259
My new favorite Applejack Moment.  
“I can’t take anymore!!”  
You and me both…