US Open Tennis 2021: Monday Night Draw TV Schedule, Start Times and Picks

Two U.S. Open champions take to Arthur Ashe Stadium on Monday night to face two very different opponents.

Novak Djokovic's quest for the Grand Slam continues against American wild card Jenson Brooksby.

Prior to the U.S. Open, Brooksby produced a single main draw victory at a major. Now, he is one of two remaining American men in the draw.

Monday's nightcap features 2019 women's singles champion Bianca Andreescu against Maria Sakkari in a battle of seeded players.

Andreescu looked strong in her first three matches, but the level of competition will go up in the round of 16 against the 2021 French Open semifinalist.

Coverage of Monday night's matches begins at 7 p.m. ET. The matches can be viewed on ESPN2 and live streams can be found on ESPN.com and the ESPN app.

Monday Night U.S. Open Matches

No. 1 Novak Djokovic vs. Jenson Brooksby

Brooksby's advancement to the round of 16 has been one of the best stories of the U.S. Open, but it should come to an end Monday night.

Djokovic's portion of the draw has opened up, and he should use the matchup with the unseeded American to fine-tune his game ahead of a potential quarterfinal clash with Matteo Berrettini.

Djokovic's game has not been flawless in the first three rounds, but he was able to recover from dropped sets against Holger Rune in the first round and Kei Nishikori in the third round.

The No. 1 seed dropped a second-set tiebreak to Rune, but then he cruised to wins in the third and fourth sets because of cramping from the teenager.

Djokovic also dropped a tiebreaker in the first set to Nishikori, but he responded by winning the next three sets by three games or more.

Brooksby battled through each of his three victories, starting with a four-set first-round win over Mikael Ymer.

The 20-year-old is coming off a five-set win over No. 21 Aslan Karatsev. He also won a four-set contest versus Taylor Fritz in the second round.

Djokovic carries the edge in quality and freshness on the court. Those two factors could play a major role in how he holds off any push from Brooksby and a crowd that will be behind the American.

Pick: Djokovic in three sets

No. 6 Bianca Andreescu vs. No. 17 Maria Sakkari

Andreescu and Sakkari will face off for the second time in their careers in the final round-of-16 match at the U.S. Open.

Andreescu won the first and only meeting with Sakkari in Miami earlier this season. That match went to three sets, and we could see a similar result play out Monday.

Both players have been in fantastic form in New York. Sakkari has not dropped a set in three rounds, while Andreescu has taken six of seven sets.

Andreescu's play at the U.S. Open has been a welcome sight after she did not make it out of the second round at each of the first three majors of the season.

The Canadian dropped a single set during her run to the U.S. Open title two years ago. She will face a more difficult run to the championship since six of the eight players left on the top half of the bracket are seeded.

Sakkari has the potential to knock out Andreescu, but she faced some trouble against higher-ranked players in the pair of tune-up tournaments.

The 17th-seeded Greek fell to Victoria Azarenka in Montreal and won four games in two sets against Angelique Kerber in Cincinnati.

The hard-court surface has also not been kind to Sakkari on the major stage. She has never made it past the fourth round at the Australian and U.S. Opens.

Andreescu's experience and previous win over Sakkari give her the edge, but it should at least be an exciting match.

Pick: Andreescu in three sets