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Australian Open 2016:
After winning Giles Simon (ATP 15, Elo 2074) in R16 in 5 sets while amassing more then 50 UFOs, Novak went to win Key Nishikori (ATP No. 7, Elo 2240), Roger Federer (ATP 3, Elo 2438) and Andy Murray (ATP 2, Elo 2390) in QF/SF/F.
This one was his hardest earned GS title: Hardest Grand Slam titles
Difficulty factor: 1.316 (meaning 31.6% harder then winning an average Open Era GS title)
 

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Next one is Australian Open 2013:
F: Andy Murray (ATP 3, Elo 2386)
SF: David Ferrer (ATP 5, Elo 2334)
QF: Tomas Berdych (ATP 6, Elo 2223)
R16: Stan Wawrinka (ATP 17, Elo 2110)
Difficulty factor: 1.211

Third one one is Australian Open 2012:
F: Rafael Nadal (ATP 2, Elo 2395)
SF: Andy Murray (ATP 4, Elo 2346)
QF: David Ferrer (ATP 5, Elo 2242)
R16: Lleyton Hewitt (ATP 181, Elo 2014)
Difficulty factor: 1.206
 

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My Top 5 would be:

1. FO 2016. Finally, finally winning the career GS after so many times getting close and hitting the roof.

2. Wimbledon 2011. The first time winning the dream of your boyhood is just so, so sweet. The celebrations in Serbia went wild and Djokovic was hailed big time in Belgrade, almost like the French world cup winners yesterday.

3. AO 2008. The outsider unexpectedly broke through in an era of Fedal's total GS dominance. A new tennis superstar was born.

4. Wimbledon 2018. Unexpected after hardship privately and physically, and the biggest career crisis with massive self-doubt.

5. US Open 2011. The sweet first and this title confirmed his dominance over Nadal on the biggest stage. The new 2011 King had arrived and been knighted. The 2010 King, who most expert predicted would dominate tennis for many years, had abdicated in a turn of events nobody had anticipated by December 2010.
 

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I'd say it's easily this Wimbledon (2018). Never before did he come into a major tournament having won nothing above 250 for almost two years, not having been to a GS semis for two years, with the lowest ranking (not counting the teenager years obviously) and so on.
 

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Maybe for him it was AO 2008, Wimb 2011, RG 2016...

For me: US Open 2015

It was pure joy watching drunk, loud and obnoxious Fed biased crowd, looking at fail of SABR
 

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Nole was insanely good that day. He was even better vs Feds at AO '16.
Yes I remember he mauled him in first 2 sets at AO, Fed was completely lost, and it was question will he totally humiliate him in third, but he let the steam out so Fed was able to regain some confidence and save his stature at least a bit.

But all that was result of UO 2015 where Federer was depicted as slight or just favorite to win tournament, where his SABR tactic was seen as something new, miraculous, when Becker was raising voice against it, when Fedr was walking through UO like nothing until he hit a brick wall.
What struck me the most was Novak's calmness in that final. His cold, no emotional display against everything and everyone a tennis player could face on a hostile ground.
Fed couldn't recover after that and Djokovic felt he owns Roger like he owned Nadal.
Luckily for Fed, Djokovic got an injury.
 
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