@liuliuliuman :
@Oberon_
If I have to guess, they are aware that the only way they can have Jeanie put in effort is that if it's something she feels personally invested.
Like here, they taunted her into a duel with the rep spot on the line (what they think will get her), and the backup plan of threatening to throw blames on her if she refuse (what ends up working)
So by covering both options, they ensure that she'll at least get a proper fight before the actual competition (not knowing that she already mastered "choke that bitch" spell before hand, Tomoe would be proud)
Even if she were somehow to lose to this kid, they can just fan her 'hate to lose' spirit to make her work harder for the next time.
Since she's won and secured her rep position, the 'keep losing' order is probably to ensure that Jeanie doesn't just suddenly go 'fuck this I'm out' if she run into an issue before the actual competition.
Also this chapter is even more reasons for me to believe her "Undine" isn't the lowest rank water spirit Undine.