5 Australian Open upsets that no one saw coming ft. Serena Williams, Novak Djokovic

Players are usually excited to perform at the Australian Open. They are fresh after a short break, and with the tournament being at the start of the season, there's no baggage on their mind.

The likes of Novak Djokovic, Roger Federer, Rafael Nadal, and Serena Williams have enjoyed tremendous success Down Under throughout their illustrious careers. However, even the greats are prone to having a bad day, or being outplayed by a peaking rival.

With that in mind, here's a look at five of the most unexpected upsets to occur at the Australian Open in recent times:

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#5. Stefanos Tsitsipas def. Roger Federer (2019)

Stefanos Tsitsipas had given an indication of what he's capable of at the Canadian Open 2018, ousting four top 10 players in a row before falling in the final to Rafael Nadal. However, he had yet to prove himself at the Majors at this point.

Tsitsipas lost in the first round of the Australian Open 2018 on his main draw debut. So when he set up a fourth-round contest against two-time defending champion Roger Federer a year later, he was the clear underdog. The Swiss ace captured the first set, though his younger rival made him work for it.

Tsitsipas' efforts in the first set made it clear that he wasn't going to go down without a fight. Matter of fact, he didn't go out in that round. He turned the tables on Federer to bring his title defense to an end. The youngster scored a 6-7 (11), 7-6, 7-6 (3), 7-5, 7-6 (5) win, heralding his arrival on one of the biggest stages of tennis. He eventually reached the semifinals, his first at a Major, where he lost to Nadal.

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#4. Fernando Verdasco def. Rafael Nadal (2016)

Rafael Nadal and Fernando Verdasco at the Australian Open 2016. (Photo: Getty)

Fernando Verdasco previously pushed Rafael Nadal to the brink in the semifinals of the Australian Open 2009. The latter emerged victorious after battling for over five hours, and went on to lift the winner's trophy. Seven years later, their paths crossed in Melbourne once again.

However, Verdasco's days as a top 10 player were behind him when they met in the first round in 2016. Nadal was also in the middle of a slump, though his position in the top 10 was still secure. Alarm bells rang when Verdasco claimed the opening set but Nadal got back on track after claiming the next two sets.

With his back up against the wall, Verdasco dug deep to take the fourth set in a tie-break, and then outplayed Nadal in the decider to script a massive upset. He won the match 7-6 (6), 4-6, 6-3, 7-6 (4), 6-2 and became the second player to beat Nadal in the first round of a Major.

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#3. Denis Istomin def. Novak Djokovic (2017)

Novak Djokovic transformed the Australian Open into his personal fortress over the years. He claimed his sixth title Down Under in 2016, and was attempting his second hat-trick at the venue in 2017.

Denis Istomin had been on the tour for a decade by the start of the Australian Open 2017. He had only one top 10 win to his name at this juncture, and the occasional good result at a Major. When he found himself face-to-face against Djokovic in the second round in Melbourne that year, no one expected anything other than a routine win for the Serb.

However, Istomin had other plans, and instead scored the most memorable win of his life. He staged an impressive comeback to beat Djokovic 7-6 (8), 5-7, 2-6, 7-6 (5), 6-4. It marked the latter's earliest exit from a Major since he fell at the same stage at Wimbledon 2008. Istomin eventually lost in the fourth round to Grigor Dimitrov.

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#2. Hyeon Chung def. Novak Djokovic (2018)

Novak Djokovic and Hyeon Chung at the Australian Open 2018. (Photo: Getty)

Following his disappointing exit from the Australian Open 2017, Novak Djokovic struggled for the rest of the season as well. He eventually shut down his season due to an injury he picked up during his Wimbledon campaign, and dropped out of the top 10.

Djokovic arrived at the Australian Open 2018 seeking his seventh title Down Under. By reaching the fourth round, he already surpassed his previous year's result. Hyeon Chung stood between him and a spot in the quarterfinals.

Chung upset fourth seed Alexander Zverev in the third round. While many expected Djokovic to win, they also felt Chung would put him through the wringer. Instead, the 21-year-old stunned the Serb and the world with a 7-6 (4), 7-5, 7-6 (3) win, and went on to make the semifinals. This would remain Djokovic's last defeat in Melbourne until his loss to Jannik Sinner in the semifinals of the Australian Open 2024.

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#1. Ana Ivanovic def. Serena Williams (2014)

Serena Williams enjoyed a career-best season in 2013, winning 11 titles from 13 finals and posting an impressive 78-4 record. She carried this form into 2014 by winning the Brisbane International at the start of the season. She arrived at the Australian Open on a 22-match winning streak, and extended it to 25 matches by reaching the fourth round in Melbourne.

Williams faced a familiar foe in the form of Ana Ivanovic in the fourth round. The latter had lost all four of her previous meetings in this rivalry in straight sets. Furthermore, she had advanced to the last eight at a Major only once since the start of 2009.

So when Williams took the opening set of their contest, no one expected what was about to unfold over the next hour. Ivanovic played some sublime tennis to take the match out of her opponent's hands, and completed a spectacular comeback to upset the American 4-6, 6-3, 6-3.

Ivanovic later lost in the semifinals, and this would remain her only win over Williams in her career. She lost their next five meetings, though three of them did go the distance. The American would triumph in Melbourne a year later.