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Background Pony #6335
@chris the lovable jerk  
I wish I could give Fleetfoot the benefit of the doubt like that, but that was also the year that Spitfire managed to beat her. Before that, their positions were reversed in the standings.
chris the lovable jerk

Okay, there’s a lot of interesting stuff to gleam from this: It’s obvious that RD is younger than the others (she mentions being the youngest in the group by a few years) and that Derpy’s part in this is… very tragic. Ironic too, as the thing that made Derpy stand out IRL was what held her back in her own life, there’s also stuff like Spitfire outdoing Lightning Dust (who doesn’t seem happy about it), and Fleetfoot actually doing better the second year… yet she looks sad, could it be she feels bad about what happened to Derpy?
Minus
King Sombra - Celebrated the 10th anniversary of The Crystal Empire!
A Lovely Nightmare Night - Celebrated the 12th anniversary of MLP:FIM!
Princess of Love - Extra special version for those who participated in the Canterlot Wedding 10th anniversary event by contributing art.
Non-Fungible Trixie -
Kinship Through Differences - Celebrated the 11th anniversary of MLP:FIM!
Philomena - For helping others attend the 2021 community collab
Twinkling Balloon - Took part in the 2021 community collab.
My Little Pony - 1992 Edition
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
Dream Come True! - Participated in the MLP 9th Anniversary Event

It's bad. In a good way!
So she got the eye issue at a young age, and then when she was a teenager she tried to have it fixed. Now we do see early Derpy with straight eyes for all but one scene in episode 1. This to me implies the surgery went well, but for whatever reason was not permanent. Nothing so far has been contradictory. But the order of the images here does make no sense at all.
Softy
Non-Fungible Trixie -
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!

@Mr grump  
@Masem
 
Actually, if you watch the whole sequence, you can see that Fleetfoot starts off 4th-tier (tin?), moves to 2nd (silver), then drops to 3rd (bronze). She’s unhappy because she performed worse than in the previous competition.
Background Pony #9764
Something happened to her and doctors have been trying to fix her eyes for ages.  
oh man…
Background Pony #08D7
Middle pic shows something happened to her and she was trying to get it fixed surgically. While she’s older, it means something happened, and the discrepancy between being able fly and being derp-eyed as a filly means she had some kind of incident.
Prof.NightJack
Equality - In our state, we do not stand out.
The End wasn't The End - Found a new home after the great exodus of 2012

Gizmonics Scientist
Part of the problem of them so rarely telling up exact time spans, we can never know the way it actully went.  
The second image might of happened some time after and the third image is when her eyes first did that.