Carlos Alcaraz vs Jan-Lennard Struff Tips, Prediction & Live Stream - Struff of legends as German aims for all-time upset

It's been a Wimbledon of upsets and I'm prepared to take a punt on Struff at $15 to pull off what would easily be the biggest shock of the tournament - and here's why.

Struff has always been competitive against Alcaraz - he's taken at least one set off the World No. 2 in all four of their previous meetings, even winning their first encounter at the French Open back in 2021. They've played in big matches, including the Madrid final in 2023 and even here at Wimbledon in 2022, which Struff led two-sets-to-one before Alcaraz edged out the fourth in a tiebreak before completing the victory in five.

Alcaraz was very average in his five-set opening round win over veteran Fabio Fognini and wasn't much better in making it past World No. 733 Oliver Tarvet in the second round. The second seed consistently goes walkabout in the early rounds of slams and rarely does things the easy way. Struff is coming off a confidence-boosting victory over Felix Auger-Aliassime and has absolutely nothing to lose. He knows he can beat Alcaraz and at these sorts of odds (and the Wimbledon we've witnessed so far this week), I'm happy to back the German to sent more shockwaves through the tournament.

As mentioned, Alcaraz leads 3-1, but Struff won their first meeting and has forced a deciding set in the subsequent three contests - including at Wimbledon in 2022, the 2023 Madrid final and their 2024 Madrid rematch in the R16.

Alcaraz has put together a dominant 44-5 record this season, coming into this clash on the back of a 20-match winning streak.

After tasting victory his opening two rounds at the All England Club, Alcaraz has now won 27 of his last 28 matches on grass, while he's now the second-fastest player in the Open Era behind Rod Laver to reach 20 match wins at Wimbledon.

The Spaniard has advanced to the final in his last five consecutive tournaments, securing titles at Roland Garros, Rome, Monte Carlo and Queen's Club. He's beaten World No. 1 Jannik Sinner in their last five meetings and he's the undisputed star of men's tennis right now.

However, for all his dominance, Alcaraz still has the tendency to make life difficult for himself - case in point, being stretched to five sets by the retiring Fabio Fognini in the first round of Wimbledon, while he also dropped sets to the likes of Damir Dzumhur and Fabian Marozsan at Roland Garros.

It's been a tough time for Struff on tour since last year's Olympics and he came into Wimbledon having won just five tour-level matches from 20 appearances in 2025.

However, what better tournament to turn things around than Wimbledon?

Struff has been to the third round at Wimbledon on four previous occasions, so he's very comfortable on the lawns and he's proved he's still a force to be reckoned with on tour.

The 35-year-old defeated Filip Misolic in four sets in the opening round before taking out Felix Auger-Aliassime in four sets in a match that spanned across two days.

Struff has registered five wins over top five players throughout his career and will be targeting another colossal upset on Friday.