Both champions have held the Norman Brookes Challenge Cup six times.
Now, Djokovic stands to end Federer’s two-year reign at Melbourne Park.
Two days after beating the Swiss in the 2008 semifinals, Djokovic would defeat Jo-Wilfried Tsonga to capture the first of his 14 majors.
“It was my first trophy that I won, first major trophy, that obviously served as a great springboard for my career,” Djokovic said on Sunday.
“It opened a lot of doors for me. It allowed me to believe in myself that I can actually win the biggest tournaments in the world, challenge the best players in the world.”
Ten years ago, Djokovic returned to Melbourne Park defending a Grand Slam title for the first time, his run ending when he succumbed to heat stress in a quarterfinal against Andy Roddick.
Often lost in the timeline of Djokovic’s long stretch of success is his wait for Grand Slam title No.2. It would not come for another three years, but from there, the floodgates opened.
“Obviously I was a youngster that had a lot of potential and talent, I was kind of working my way up,” he said. “But winning a slam is completely different.
“So that was quite a unique experience for me … I have not won any slam for, yeah, two, three years. It took me a while to really make that breakthrough again.”
Not since his maiden Australian Open title run in 2008 had Djokovic fallen before the quarterfinals in consecutive campaigns. But after suffering one of the greatest upsets in slam history, falling to Denis Istomin in the second round in Melbourne in 2017, South Korea’s Hyeon Chung pulled off the improbable when he denied an underdone Djokovic 12 months ago in the last 16.
A once formidable mental fortress, a 20th-seeded Djokovic then capitulated in a Roland Garros quarterfinal against world No.72 Marco Cecchinato in May.
Good thing he backflipped on a decision to skip the subsequent grass-court swing.
Little more than three months later, Djokovic had picked up back-to-back slams at Wimbledon and the US Open, and went on to finish the year back at No.1.
Fourteen years into his career, there are parallels that can be drawn between the struggle to notch up Grand Slam No.2 and returning to the major winner’s fold at Wimbledon 2018, after two years of coming up short.
“If you won it once, you always believe that you can win it again,” he said. “So you're approaching … slams knowing in the back of their mind that they can actually win it again.
“It raises expectations, which raises pressure, and you have to deal with that. But it comes with, I think, experience and time where you start to feel more comfortable. You start to embrace it more and accept it as part of your life.”
“It's unbelievable to beat the No.1 player in the world, probably the best this court has seen.”
This was the post-match reaction from a 20-year-old Serb named Novak Djokovic, after he snapped Roger Federer’s 19-match winning streak at Melbourne Park.
That was in 2008, after a night semifinal at Rod Laver Arena.
How telling that 11 years later, Djokovic and Federer – the equal two most successful players on that same court – enter AO 2019 as the pre-tournament favourites to meet in the final.