How will Rafael Nadal do in his first match on grass in three years? Can Felix Auger-Aliassime overcome the net-rushing game of Eastbourne finalist Maxime Cressy? It’s going to be an exciting first few days of The Championships with a slew of fantastic first-round match-ups on the men’s side—here are just five of the most notable ones to keep an eye on:

[5] Carlos Alcaraz (ESP) vs Jan-Lennard Struff (GER) [Struff leads 1-0]
Alcaraz, who only just turned 19 last month, has already proven he’s a world-beater on the other two surfaces—he already has a Masters 1000 title on hard courts in Miami this year, and he’s won three titles on clay this year, including another Masters 1000 in Madrid. He’s also been to Grand Slam quarterfinals on both surfaces, at the US Open last year and Roland Garros this year.

His grass-court prowess will immediately be put to the test against Struff in his opening match at Wimbledon, as Struff’s big serve and groundstrokes can overpower anyone when he’s on—he has 10 career Top 10 wins, all between 2016 and 2021, and the biggest one actually came on grass with a first-round upset over then-No. 2 Daniil Medvedev in Halle last year.

The German also beat Alcaraz in their only previous meeting, 6-4, 7-6 (3), 6-2, in the first round of Roland Garros last year.

The Spaniard will be playing his first match since falling to Alexander Zverev in the quarterfinals of Roland Garros this year—he withdrew from his only scheduled grass-court lead-up event at Queen’s Club due to an elbow injury.

[6] Felix Auger-Aliassime (CAN) vs Maxime Cressy (USA) [first meeting]
Auger-Aliassime has shown he has a penchant for grass, not only reaching two finals on the surface (Stuttgart in 2019 and 2021) and his first Grand Slam quarterfinal at Wimbledon a year ago, but also coming to the All England Club this year off of a strong lead-up season, reaching the semifinals of ’s-Hertogenbosch and the quarterfinals in Halle. He has a 22-8 career record on grass.

His first opponent here could be very dangerous, though—Cressy, one of the few players on the tour who embraces serve-and-volleying, fell first round in his first two grass-court lead-up events in Stuttgart and Halle, but just made his second ATP final of the year on the lawns on Eastbourne, barely falling to American No. 1 Taylor Fritz in the final, 6-2, 6-7 (4), 7-6 (4).

Cressy is 0-4 against Top 10 players, which isn’t a great sign as he takes on the world No. 9, but he does have three career Top 20 wins, and two of them came on grass—this past week, actually, as he took out No. 18 Reilly Opelka and No. 12 Cam Norrie en route to the final in Eastbourne.

[2] Rafael Nadal (ESP) vs Francisco Cerundolo (ARG) [first meeting]
This one isn’t so much about Cerundolo—the young Argentine, who reached his first Masters 1000 semifinal in Miami this year, has only played three career matches on grass, going 1-2.

It’s more about Nadal making his return to grass for the first time in three years—this will be his first match on the surface since falling to Roger Federer in the semifinals of Wimbledon in 2019, after the 2020 grass-court season was cancelled due to the COVID-19 pandemic and he had to miss this part of the season last year due to a chronic foot injury.

Apart from a tough stretch between 2012 and 2017 where he didn’t make the quarterfinals once, Nadal has always gone very deep at Wimbledon, winning two titles (2008 and 2010), reaching another three finals (2006, 2007 and 2011) and another two semifinals (2018 and 2019). He’s 14-0 at the majors so far this year and is hoping to make that 15-0 as he faces Cerundolo for the first time.

Auger-Aliassime reached his first major quarterfinal at Wimbledon a year ago, taking out Alexander Zverev along the way.

Auger-Aliassime reached his first major quarterfinal at Wimbledon a year ago, taking out Alexander Zverev along the way.


[10] Jannik Sinner (ITA) vs [WC] Stan Wawrinka (SUI) [Wawrinka leads 2-0]
As Wawrinka continues to work his way back up the rankings after a string of injuries over the last several years—most recently a foot injury that put him out for most of last year—he’s going to be a dangerous unseeded floater in any draw, and in this case, he floated into Sinner’s draw.

Sinner has had big results on hard and clay, reaching Grand Slam quarterfinals on both surfaces (Roland Garros in 2020 and Australian Open this year), but he’s struggled to break through on grass, going 0-4 in tour-level matches on the surface. Wawrinka may have won all three of his majors on the other surfaces, but he’s a two-time quarterfinalist at Wimbledon in 2014 and 2015. The Swiss also won both of the pair’s previous meetings, both in 2019, at the US Open and Antwerp.

The former No. 3 will be going for his first win over a Top 15 player since 2020 (he defeated a No. 8-ranked Andrey Rublev at the Masters 1000 event in Paris at the end of the year that year).

[8] Matteo Berrettini (ITA) vs Cristian Garin (CHI) [Berrettini leads 2-1]
Garin may primarily be known for his results on clay, winning all five of his career ATP titles on the surface and reaching the second week of a major for the first time on it too at Roland Garros last year—but the Chilean, who was ranked in the Top 20 as recently as February, also made the second week of Wimbledon last year before falling to eventual champion Novak Djokovic in the fourth round.

Berrettini, meanwhile, is one of the best grass-court players out there—he’s won 32 of his last 35 matches on grass since the start of 2019, which not only includes reaching his first major final at Wimbledon last year, but also four ATP titles on the surface at Stuttgart in 2019, Queen’s Club in 2021 and Stuttgart and Queen’s Club this year.

Garin won the pair’s first meeting in Munich in 2019, and Berrettini has gotten the better of the Chilean in their last two meetings, at Shanghai in 2019 and Madrid last year.