Novak Djokovic lost his first career Grand Slam final at the US Open, then won his second at the Australian Open. And look where he is now, more than a dozen years later: One victory from a ninth championship at Melbourne Park and his 18th major title overall, which would put him two behind rivals Roger Federer and Rafael Nadal for the most by a man in tennis history. Daniil Medvedev also lost his first career Grand Slam final at the US Open. And now he will try to win in his second, which comes at the Australian Open on Sunday — against Djokovic. (More Tennis News)