2008: Julie Coin defeats Ana Ivanovic
After surviving a scare in the first round against Vera Dushevina, number one seed Ana Ivanovic crashed in second round. She lost to french qualifier Julie Coin, ranked 188 and making her Grand Slam debut.
Ivanovic, who had been bothered by a thumb injury, cited fatigue and lack of preparation to explain the so-called “biggest upset in US Open history”.
Julie Coin’s magical run ended against former number one Amelie Mauresmo in the third round.
Until Coin’s win, the top seed at the US Open had not lost earlier than the third round when Billie Jean King was ousted in the 1973 tournament.

2005: Ekaterina Bychkova defeats Svetlana Kuznetsova
Defending champion Svetlana Kuznetsova lost to number 97 Elena Bychkova in the first round, becoming the first female defending champion to lose in the first round.

I tried my best, it wasn’t my day. What do I do? Kill myself? No I don’t. Just take positive things out of this and maybe I’ll try to learn

Following the US Open, Kuznetsova played just 4 matches during the remainding of the year, winning 2 of them.
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Much better than Justine Henin’s outfit. But leggings???