The American lefty has won a trio of five-setters to reach the second week, holding off Denis Shapovalov Saturday.

WIMBLEDON—“We’re back, big dog,” were the words Ben Shelton directed towards his father Bryan this afternoon on Court 1 at Wimbledon. Having just beaten fellow lefty Denis Shapovalov, Ben had equaled Bryan’s feat of reaching Wimbledon’s round of 16, a result he generated back in 1994.

Father and son both got that far the hard way. Thirty years ago, two of the 120^th-ranked Bryan’s three wins were five-setters. Oddly enough, his most routine victory was a straight-set, first-round win over the second seed, 1991 Wimbledon champion Michael Stich. “Pretty cool,” said Ben following today’s match. “I think a lot more impressive that he was able to do it back in the day, beating the No. 2 player in the world . . . But, yeah, really happy that we get to kind of share this moment together again. Not again, but together for the first time.”

This time around, all three of Ben’s victories thus far have gone the distance. Today’s effort began on Friday but was suspended due to rain, with Shapovalov serving at 2-3 in the first set. It resumed Saturday afternoon and, in the end, lasted four minutes past the three-hour mark, Shelton earning a 6-7 (4), 6-2, 6-4, 4-6, 6-2 victory versus an opponent who personifies the word “streaky” as much as anyone in contemporary pro tennis.

Said Shelton, “Today Shapo started doing a really good job in the fourth set of returning my serve, finding a way to neutralize, so I had to change it up. In the fifth set I served almost every serve into the body and serve and volleyed. I think that’s the part that I like the most about it: the game within the game.” All told, Shelton went 52 of 78 at the net, including a sparkling 11 of 15 in the final set. To a great degree, it was a tactic lifted from his father’s era.

For many players, when one of the parents has been a pro, tennis is the family business, the highly accomplished father or mother keen to dispense wisdom and memories. It wasn’t that way in the Shelton household. Speaking about Bryan, Ben said, “Yeah, he’s not really a guy who likes to talk about himself. So he didn’t really volunteer that information when I was younger. And I was playing other sports and could care less about tennis and his playing days when I was younger. That’s not something we really talked about.”

Things changed, though, when Ben played for Bryan at the University of Florida. “That was tough because there’s 11 other guys on the team,” said Shelton. “I’m the coach’s son, so he has to show that there’s no favoritism, which I understand. But also, I’m running more sprints than everyone else when I do something wrong or show up late. I’m getting chewed out for more. If I lose a match, it’s a bigger deal than everyone else, which I understand why he had to do that to keep the team in the right place. So things were much more difficult than when we got out on tour.”

The biggest challenge in tennis [is] playing the top-ranked player in the world. But I’m never somebody to be scared going into a match or feel unprepared. I’m always confident in my abilities no matter who is on the other side of the net. —Ben Shelton on facing Jannik Sinner in the round of 16

But as Ben’s pro career evolved, he realized his father had a distinct and useful set of assets. “So after not working with him or traveling with him for eight months while he still had the job at the university,” said Shelton, “and he came out on tour with me, I kind of really kind of really started to appreciate everything he was bringing to the table for me because I was missing it during that time.”

Time has also worked in Shelton’s favor. With mid-match coaching now permitted, he and Bryan are able to replicate the coach-player connection that they had during college matches. Better yet, in this case there are no other players Bryan needs to pay attention to. Said Shelton, “I think that with the new coaching rule, I think that the information that he’s able to give me during the match, he can help keep me in the right state of mind. Yeah, I’ve really enjoyed the kind of back and forth that we’ve been able to have during the matches.”

Once again, Shelton has proven himself a man who enjoys rising to the occasion. In last summer’s North American hard-court season, he went a mere 2-4—but then reached the semis of the US Open. During the pre-Wimbledon grass season, Shelton won just one of four matches. His victories this week are only the second time this year Shelton has won three matches at a specific event.

Amid various delays, so far during The Championships, Shelton has walked on to the court to play singles matches on five of the tournament’s first six days. Tomorrow will be the sixth of seven, this time versus first-seeded Jannik Sinner. These two have played one another three times. Shelton won the first, squeaking out a third-set tiebreaker last year in Shanghai. Sinner has won the last two without the loss of a set.

“I think it’s a great opportunity for me, a great challenge and test,” said Shelton. “The biggest challenge in tennis [is] playing the top-ranked player in the world. But I’m never somebody to be scared going into a match or feel unprepared. I’m always confident in my abilities no matter who is on the other side of the net. I’m going to go out there and, like I said, try to problem-solve, figure things out as it goes. Yeah, just compete as hard as I can.”

The presence of Bryan, of course, is another strong X factor. “I think it’s really cool for us to be able to share this moment together,” said Shelton. “It’s something that I don’t know if we thought that we would be in this position at this point in our lives, but really just grateful for everything that’s happened so far. Yeah, going to continue to work and try to move forward.”