Wimbledon - Round of 16 (Day 1) Predictions

Jannik Sinner and Daniil Medvedev headline Wimbledon action on Sunday, with blockbuster matchups slated against Shelton and Dimitrov respectively. Defending champ Alcaraz and Paul also take to court.

Paul vs Bautista Agut

Except for his tense tussle with Otto Virtanen in Round 2, Tommy Paul's run to the second week here at Wimbledon has been relatively straightforward. The American has carried the momentum from his first ATP 500 title at Queens to the freshly mowed lawns of SW19 with ease. Although he looked well on his way in his opener against clay-courter Pedro Martinez, Paul experienced a blip in the third set, quickly regrouping to close out the fourth 6-3. However, the second round saw an ultimate scare in the form of Finnish thunderbolt Virtanen. The 6'4" man has a cracking serve paired with lethal groundstrokes, and when he finds his stride, is almost unplayable. Virtanen brushed aside Max Purcell - last week's Eastbourne finalist - for the loss of just seven games, and was playing at a scary level in the second round as he clinched a 2-set-to-1 lead against Paul. However, like all good players, the 12th seed did nothing special; he simply waited for a dip in level. And it came. As errors leaked into Otto's baseline game and his serving numbers tapered off, Tommy clung on and grabbed the next two sets to win the match. It was daylight robbery. And although many were speculating an even tougher battle in his next round against Alexander Bublik, the Kazakh simply didn't show up mentally; instead, it was a breezy straight-set display from the American.

Bautista Agut had an emotional triumph against Fabio Fognini in his last round. At 36 years of age, the Spaniard may be reaching the denouement of his career - but his doggedness is certainly still here. Trailing 2 sets to 1 before a rain delay interrupted play, RBA came out the next day with renewed confidence, taking the fourth set in a tiebreak and closing the match at 6-4. His trademark determination and unrelenting brand of tennis saw him through. For Fognini - another veteran of the game - it was disappointment, who was looking to claw his way to the fourth round of Wimbledon for the first time in his career after an impressive win over 8th seed Casper Ruud in Round 2. Roberto has also earned routine wins over Marterer and Sonego so far, dropping only one set in his first two rounds.

If this was a first-round match, I would expect it to be much closer. However, Bautista Agut's fitness levels will be all but depleted considering his time on court from yesterday and his age. Furthermore, their recent head-to-head is also in Paul's favour; while the Spaniard took their first three meetings, Paul has turned it around in their last two - including a four-set win in the fourth round of the Australian Open in 2023. Expect the American to overwhelm RBA's steadiness here.

Prediction: Paul in 4

Alcaraz vs Humbert

Ugo Humbert is rediscovering his form this week. The Frenchman is into the Round of 16 at a Grand Slam for the first time since Wimbledon 2019 - exactly five years ago. Grass has always theoretically been Ugo's best surface, what with his lefty serve and clean, wristy strokes. However, it hasn't always worked out, with Humbert's only big highlight on the surface coming in 2022 with a trophy at Halle. But there have been encouraging signs this week. After a gruelling 5-set marathon against Shevchenko, the 16th seed was dominant in his second round against the struggling Van de Zandschulp. The Dutchman, who made a miraculous trip to the quarterfinals of the 2022 US Open and was the only man to take a set from eventual champion Daniil Medvedev, is stuck in a huge rut of form. In Humbert's next round, he took on the red-hot Nakashima. After a poor 2023, Brandon stormed through the Wimbledon draw with comfortable wins against Baez and Thompson. While the Frenchman took the first two sets in this match, he lost the third set tiebreaker, and just before the pair were headed to one in the fourth, rain pelted down. But the Humbert regrouped the following morning and won the meeting with his signature French flair.

Meanwhile, Carlos Alcaraz has certainly not been in his best form this year. After a tentative opening round against the relatively unknown Estonian qualifier Lajal, he was again tested in the first set against Vukic. However, even though the Spaniard managed to win these matches in straights, he was pushed to the limit by a resurgent Frances Tiafoe in their Round 3 encounter. Down two sets to one, the World Number 3 was playing some uncharacteristically unforced-error-riddled tennis. His exuberance and aura were lacklustre, his celebrations quieter and more dejected, and his usually venomous forehand was spraying mistakes. But as the fourth set bled into a tiebreak, the going got tough - and so Alcaraz got going. Carlos entered lockdown mode, striking his groundstrokes with menacing authority and committing very few errors. Clinching the set with a roar, the Spaniard didn't stop there, racing to the finish line as Tiafoe faltered. Alcaraz now improves to an astonishing 12-1 record in fifth sets.

I am picking Alcaraz to win this one safely. Humbert has been underwhelming this grass season, and Alcaraz's assault will leave him flustered. Although Humbert can be impressive on the front foot, his defence is often weaker; Carlos's barrage of aggression will only expose this. Ugo might nab a set given how scratchy the third seed has been; however, Alcaraz will cruise in all other departments.

Prediction: Alcaraz in 4

Sinner vs Shelton

This is arguably the match of the day. Fireworks will fly in a Fire vs Ice matchup, as two polar opposites of the game collide. While Shelton has the bigger serve, his game is more erratic, while Sinner represents a more steady, measured brand of tennis. But make no mistake; neither of these guys lacks in terms of power. The power on display here will be off the charts, with the sound of the ball coming off the racket like a bullet fired from a rifle.

Sinner has been his usual routine self this week. While he was stretched to four sets by Hanfmann and Berrettini - the latter of whom with he played one of the matches of the tournament so far - he was clinical in dismantling the underpowered Miomir Kecmanovic in three sets. In his match against Matteo, Jannik showed just why he's considered one of the most clutch players right now. As errors flowed from the Berrettini racket, Sinner turned it up a notch and snatched all three tiebreaks from the supposedly better server.

Shelton's serve will be much mightier than Matteo's. The ebullient American - who recently thumped down the fastest-ever serve at Wimbledon - has had his fair share of match time. All three of his rounds have been taken to five sets, and while his struggles against qualifier Mattia Bellucci were concerning, he did very well to come through the dangerous likes of Harris and Shapovalov. Denis, as always, made some head-scratching errors, with the Shelton kick serve to the Shapo backhand proving to be ultra-effective. As the Canadian double-faulted his way to defeat, Ben showed us all his elite mentality.

But he will need more than just mentality to topple the top seed. While his otherwordly ball-striking will give Jannik fierce competition for a set, I'm choosing the Italian to outlast and outhit the American in the end.

Prediction: Sinner in 4

Medvedev vs Dimitrov

Both of these men have flown under the radar here at SW19. Daniil Medvedev has been unwavering so far in his first three matches. With an assertive display against Kovacevic in his opener, however, Medvedev was in hot water in Round 2. Frenchman Alexandre Muller had the fifth seed on the ropes, taking the first set tiebreak convincingly and breaking the Russian early in the second. Soon enough though, Daniil recovered, fending off a break point and clinching the second set with fighting spirit. Although many expected Medvedev to cruise from there, Muller put up a hell of a fight, ultimately falling short. But this match raised many question marks for Medvedev going into his third-round match. Jan-Lennard Struff, always a dark horse - especially on the quickness of the grass - awaited. A large portion of tennis fans actually expected Struff to pull off the upset. But Medvedev, solid as ever, proved them all wrong. He raced out of the blocks to take the first two sets 6-1, 6-3, gliding across the court to absorb and redirect Struff's fiery pace. But soon, things started unravelling; the German forayed more and more into the net and started finishing points with great control. Then, perhaps fortunately for Medvedev, the rain made a charge, and all play for the day on the outside courts ceased. The next day, Medvedev closed out a magnificent tiebreaker in the searing sunlight, hooking passing shots left, right and centre from seemingly impossible positions. Although many expected otherwise, it was smooth sailing for Medvedev as he approached his fourth round.

Grigor Dimitrov has also been scintillating at the All-England Club so far. After a clean display against Dusan Lajovic, the Bulgarian found himself down two sets to love against retrieving skills of JC Shang. But for just the second time in his career, Dimitrov came back to win the next three sets in fine style as Shang's body let him down. In the Round of 32, Grigor came up against some stiff competition in an inspired Gael Monfils. The Frenchman had reached the final in Mallorca and was looking to translate this form into a fourth-round appearance at his least fruitful slam. However, Gael's passiveness saw his downfall yet again, as Dimitrov's riskier style of tennis paid dividends.

This matchup has been a treat in recent times. Although the 6'6" Russian leads the H2H 7-3, their two meetings in the latter half of 2023 have been split, with each encounter going down to the wire. Grigor has all the right tools to unsettle Medvedev, with his nasty slice and wicked variety sure to cause the World Number 5 trouble on the grass. This match definitely has the potential to go the distance. But can Grigor maintain his level over five sets? Ultimately, I am backing Medvedev's solidness, slam pedigree and fitness to get the better of Dimitrov yet again.

Prediction: Medvedev in 5