By Flint Wheeler

Two questions loom as the final Slam of the year begins, both of them concerning 17-time major champions. Can Serena Williams put a lackluster year at the majors behind her and defend her US Open crown? And can Roger Federer turn back the clock for two weeks and win his 18th major at the ripe old age of 33?

Federer nearly pulled it off at Wimbledon last month with a riveting comeback before Novak Djokovic steadied himself in the fifth set to emerge victorious. Djokovic is the oddsmakers’ favorite at the Open, and despite his hard-court prowess (five of his seven majors have come on hard), he has looked out of sorts all summer, losing early in warm-up tournaments to Jo-Wilfried Tsonga and Tommy Robredo (Who?). The best-of-five matches at the US Open will steady him with the break of Rafael Nadal absent nursing a wrist injury, Djokovic will be the toughest out over the next two weeks. A potential quarterfinal matchup with 2012 US Open champ Andy Murray tantalizes, but Murray’s draw is filled with dangerous players. The Scot continues to struggle closing out tight matches since his return from back injury. For Murray, making the quarters will be accomplishment enough.

It’s hard to bet against Serena Williams, but her lackluster results at the majors (particularly that bizarre retirement from her Wimbledon doubles match) has some speculating another early exit in New York. Serena has not advanced past the fourth round of a Slam this year; she could face Sam Stosur (her 2011 US Open conqueror) in the round of 16, Ana Ivanovic in the quarters and Eugenie Bouchard in the semis–all that and Serena should still be favored to win it all. Barring injury, it boggles the mind that Serena would let a fourth chance for late-career glory slip away this year.

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Ana Ivanovic is hoping she can spoil Williams’ ambitions for an 18th major. She did so in Australia, and that win prefaced a remarkable season in which the long-struggling Serbian finally rediscovered the forehand and footwork that led her to a French Open title in 2008. Ivanovic leads the tour with 47 wins and if she can overcome a tricky first-round match against big-hitting American Alison Riske, she’ll enjoy an uncomplicated road to the quarters and a rematch against a familiar foe in Williams.

Another familiar foe for Serena Williams, Maria Sharapova, has landed on the opposite side of the draw. Sharapova should be relieved; the reigning French Open champ has failed to beat Serena in a decade. Like Djokovic this summer, Sharapova has played erratically in North America, and she let a marathon match against Ivanovic slip away after holding two match points. It’s been eight years since Sharapova won in New York; Sharapova has failed to reach the final since. Her high ball toss, erratic second serve and low-margin game can wobble with the gusty winds that blow around Arthur Ashe stadium. She’ll need to summon her remarkable fight, and frankly, play better if she stands any chance of winning.

Halep is ready to march through the bottom half of the draw if Sharapova falters. The roller-coaster world no. 2 has not wowed this summer, but she has backed up her breakout 2013 with much improved results at the biggest tournaments. Her balanced, balletic tennis makes the game look easy and she remains tough to beat for anyone not named Maria Sharapova, who’s won all three matches they’ve played this year. Before their highly anticipated French Open rematch, Halep may need to overcome talented slugger Garbine Muguruza and two-time US Open champion Venus Williams, who’s playing her best tennis in years and loves to fight on Arthur Ashe.

At 34 (Yep, 34!) Venus Williams is as much of a contender as heralded youngsters Eugenie Bouchard, Grigor Dimitrov and Milos Raonic. Of the three Bouchard has enjoyed the best results but she has not coped well over the last month with the glare of the public eye and the pressure of being the WTA’s next-in-waiting. Both Dimitrov and Raonic have the game to contend but it will take a herculean effort for either of them to upset Federer or Djokovic and reach the final. A more realistic spoiler to Djokovic’s aspirations for a fifth straight US Open final is Stanislas Wawrinka. He nearly toppled the Serb last year and finally outlasted Djokovic in a classic match in Australia this year on the way to his surprise Slam. Wawrinka has the game and has been in this position before.

Wimbledon champ Petra Kvitova has all the power and talent to go far but the hazy New York City heat has never agreed with her asthma, though she is coming off a win in New Haven last week. Svetlana Kuznetsova, a winner here in 2004, and past finalists Caroline Wozniacki and Victoria Azarenka all play fantastic hard-court tennis but enter the tournament under the radar. That could all change with one or two big upsets. Lastly, apart from the Williams sisters and doubles stars the Bryan brothers, don’t expect another American to be in the mix late in the tournament. Though the US Open may seem wide open with Nadal’s absence and Serena’s struggles, a veteran champion will likely reign supreme on both sides.