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Poptard
Every pony has fans - Derpi Supporter
Silver Bit -
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Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
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The End wasn't The End - Found a new home after the great exodus of 2012

The Tastiest
@SorryNeverSorry
 
I agree with you on the first two, the second one most likely leading to the first. However, she seems plenty aware of most of the threats she’s faced and deals with appropriately, with Chrysalis and the Storm King the notable exceptions.
SorryNeverSorry

Offensive. Please ban.
@Poptard  
I think the reason Celestia loses so is for several reasons. One, she’s about a thousand years out of practice. Two, she most likely detests violence, or at least inflicting violence herself. Three, it might be one of those “Good can’t comprehend evil” things, where she fails to see evil’s machinations until things become dire.
Background Pony #FCFF
@Poptard  
Wellp if you’re with me and the minority that considered the few canon comics as-… well canon, she’s won a good few in those.
Poptard
Every pony has fans - Derpi Supporter
Silver Bit -
Diamond -
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
Happy Derpy! -
Silver Supporter -
The End wasn't The End - Found a new home after the great exodus of 2012

The Tastiest
Unfortunately, I don’t think Celestia’s ever shown to actually win a fight. I’m hesitant to count her vs. Nightmare moon because she used an external weapon to essentially pause the battle for a thousand years.
 
But that’s fine. It’s not her job to fight. That’s the Royal Guard’s duty, and we’re all aware of their flawless track record.