Maybe they didn't legitimately win the first time. I imagine it as more of a "redefeat Bush" thing. Like, defeat Bush, "again".
Maybe it's just that they never actually won before. It could mean, "We won this year and if we had competed before we would have won then too.".
I think perhaps it indicates the endorsement of the baby from the show Dinosaurs.
I like to think of it as that they heard an incredulous "Again!?" every time they mentioned their victory. Eventually they decided to preempt the disbelief by writing it down themselves on the window.
Bullwinkle: Hey Rocky, watch me win the Great Aussie pie competition!Rocky: Again?!
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