Three to See, Madrid Day 6: Novak Djokovic vs. Gael Monfils; Jessica Pegula vs. Bianca Andreescu; Denis Shapovalov vs. Andy Murray

Each day during the Mutua Madrid Open, we'll preview three must-see matches.

Novak Djokovic vs. Gael Monfils

“Nobody beats Vitas Gerulaitis 17 times in a row,” Vitas Gerulaitis famously said after finally defeating Jimmy Connors in his 17th try. Unfortunately for Monfils, he can’t say the same thing, because Djokovic is 17-0 against him. Monfils has been close: He lost 7-5 in the fifth set in their first meeting, back in 2005. He has twice lost 7-6 in the third set. And he had three match points the last time they played, in Dubai in 2020. Is this the day, after 17 losses and 17 years, that the Frenchman breaks through?

It’s possible. Djokovic, who will turn 35 in a few weeks, has struggled physically in his 2022 comeback so far; he won a total of one game in his third-set losses to Alejandro Davidovich Fokina and Andrey Rublev, in Monte Carlo and Belgrade. But Monfils, who turned 35 last December, hasn’t done much since reaching the quarterfinals at the Australian Open. Djokovic has won Madrid three times, and he should feel some urgency about putting in a good result this time. Unfortunately, that means the Frenchman probably won’t have a chance to one-up Gerulaitis and say, “Nobody beats Gael Monfils 18 times in a row.” Winner: Djokovic

Jessica Pegula vs. Bianca Andreescu

The only meeting between the American and the Canadian came in an Oracle Challenger event in January 2019. They’ve both come a long way since. Two months after that, Andreescu shocked the world by winning Indian Wells; a few months later, Pegula shocked a somewhat smaller portion of the world by winning the Citi Open.

Over the last three years, Pegula has established herself as a steady and reliable competitor, and a regular denizen of the Top 20. Andreescu, meanwhile, has done the opposite. She scaled the game’s highest heights when she beat Serena Williams in a US Open final, but she has also spent more time sidelined by injury than any other star player. “Bianca is back!” are words we hear every six months or so, and we heard them again after her 6-1, 6-1 stampede over Danielle Collins in her first match in Madrid. Pegula should make her work more, but Andreescu at her best is the better player. Winner: Andreescu

Denis Shapovalov vs. Andy Murray

Murray pronounced himself happy with his game, with his tactics, and with his movement in his first-round win over Dominic Thiem. He also said he was happy with the “lots and lots of work” he has put in over the last two months. But will it be enough against Shapovalov in the second round? Murray has lost at this stage at his last five tournaments, and he went out in lopsided fashion to Shapovalov in their only previous meeting, last year at Wimbledon.

Murray did look pretty good against Thiem, and maybe clay will be a better surface than grass for him to face Shapovalov’s lefty serve and first-strike ground-stroke attack. But even with former Grand Slam champions, sometimes the current rankings don’t lie. Shapovalov is No. 16; Murray is No. 78. Winner: Shapovalov