20 for 20: No. 20, Pennetta d. Vinci, 2015 U.S. Open

Last year, for the 50th anniversary of TENNIS Magazine, we focused on the past. Given the tome of stories we’d told, and the trove of players and matches we’d witnessed over the past half-century, it was only natural to look back.

And it was comical to even consider doing something similar this year, for the 20th anniversary of TENNIS.com. So we’re taking the opposite approach, and instead focusing on the future. All throughout the week, we’ll be talking about what’s next for the sport, the website and much more.

It wouldn’t be an anniversary, though, without a countdown. But how do you count down events that haven’t yet happened? By predicting what will come to be.

With that said, we present TENNIS.com’s 20 for 20: Twenty matches that we’ll still be talking about twenty years from now. We’ve restricted this list to matches that have taken place in the last 10 years—or, as 20 for 20 author Steve Tignor has put it, “The Golden Decade.” (If you haven’t read our 50th Anniversary Moments or Tournament of Champions, also written by Steve, I implore you to do so.)

It has been a bountiful time for tennis since TENNIS.com’s inception, and it’s anyone’s guess what the next 20 years will bring. But we believe that each of these matches will sustain the test of time.—Ed McGrogan, Senior Editor

The 2015 U.S. Open women’s final had been sold out for weeks, and some fans paid thousands of dollars for a seat. This was the night, they all believed, when they would watch Serena Williams win the first calendar-year Grand Slam since 1988.

On the appointed evening, though, the fans filled the seats in Arthur Ashe Stadium, but Williams was nowhere to be found. Two days earlier, she had been stunned by Roberta Vinci in the semifinals, in the year’s biggest upset. Instead of seeing history in the final, the crowd was treated to an evening of family.

Vinci and Flavia Pennetta, 32 and 33, respectively, were fellow Italians who had been playing tennis together for two decades. They treated this match less like a one-on-one showdown and more like a mutual celebration of 20 years well spent. If that sounds dull, it wasn’t; rather than drama, the night was filled with good vibes as these two women moved each other around with their stylish games.

“Before the match, we say it doesn’t matter,” Pennetta told reporters afterward. “We’re gonna win. It’s going to be a big win for both of us. It’s going to be a really big win for both of us.”

When it was over, Pennetta and Vinci sat on the same side of the net and laughed together as they waited for the trophy ceremony to begin. But their talk wasn’t just idle gossip. Pennetta had news for Vinci: She was about to announce her retirement. A few minutes later, she told her secret to the world. Pennetta had walked away on top, after her first and only Grand Slam singles title. On the way out, she and Vinci had shown the world how much camaraderie a one-on-one sport can contain.

The fans had expected something special, and that’s what they saw.