Eh, personally I interpreted the line as ‘Look, we don’t have to literally win 100% of the games. As long as we’re seen as the best school out there, and any losses are written off as ‘bad luck’ or such, it’s fine.’  
It’s rare for a reputation to be entirely shattered just from one loss; Sports teams, in all kinds of sports, lose to ‘worse’ teams all the time, for example!
 
It doesn’t really change much; They still need to do everything they can to win, in the name of ‘Reputation!’  
But at least it means that if someone’s bowstring snaps, or the bike has a malfunction, or a wheel comes off the skating shoes… She might still get what she wants, as long as it looks like they were going to win before the accident.

Mmmm…..Everything

@Animegx43
 
Cinch: …What.
 
Discord: I’m not kidding. What you’re doing is illegal. Instead, you could have gone after her parents, but you’re pushing legal boundaries into borderline…what’s your age?
 
Twilight: Seventeen.
 
Discord: Borderline child stalking charges.

@wildrook  
Discord: How could you blackmail this student? Her parents are the ones you want to get the dirt on.

@Animegx43
 
You forgot the part where my babysitter’s Aunts know the Superintendent personally, and he knows about the blackmailing.
 
Discord: Evening, Miss Cinch.

@Ebonysdagger  
Please, I already control the school bored.

@Animegx43  
Before or after we’ve jointly reported you blackmailing a student to the school board?

@Ebonysdagger  
In that case, she won’t be Dean if we don’t win either.

Twilight: The part where you blackmail me into doing this mostly. Indeed, I think I could speak to the Dean of this school about that. You know she is more or less family, right?

“I, principal Cinch, have only one thought in my head…to be victorious!”

All of it.

That’s the problem indeed.