Daniil Medvedev's upset of Jannik Sinner only the start of daunting path to first Wimbledon title

Daniil Medvedev slayed one dragon in his pursuit of a first Wimbledon championship on Tuesday. Can he down two more?

Medvedev defeated the No. 1 player in men's tennis, Jannik Sinner, in a five-set nail-biter, 6-7, 6-4, 7-6, 2-6, 6-3, which could be the start of an arduous three-match streak for the 2021 U.S. Open winner.

He plays world No. 2 Carlos Alcaraz in the semifinals. Alcaraz defeated Tommy Paul in four sets, 5-7, 6-4, 6-2, 6-2 on Tuesday.

The two have met six times previously, with Alcaraz holding a 4-2 advantage.

It's the second consecutive year they've met in the semis at Wimbledon. Last year, Alcaraz defeated Medvedev in straight sets, 6-3, 6-3, 6-3, to get revenge for a 2021 Wimbledon Round of 64 loss.

If Medvedev gets past Alcaraz, he could potentially face Novak Djokovic in the finals. The 24-time grand slam winner plays No. 9 Alex De Minaur in the quarterfinals. Djokovic's path to the finals includes a semifinal match with either No. 13 Taylor Fritz or No. 25 Lorenzo Musetti.

Medvedev and Djokovic also met at the 2023 U.S. Open finals, which Djokovic won, 6-3, 7-6, 6-3.

Overall, Djokovic is 10-5 against Medvedev, including wins in five of their last six meetings.

After winning the 2021 U.S. Open, Medvedev has come painfully close on multiple occasions to winning a second grand slam to no avail.

At the 2022 and 2024 Australian Open, Medvedev won the first two sets before dropping three consecutive to lose.

That most recent Aussie Open loss was against Sinner, and Medvedev might have to get past a pair of other rivals to finally score his Wimbledon breakthrough.