The WTA Finals Singapore Presented by SC Global will kick off on Sunday with a pair of blockbuster singles tilts. Plus there’s the Rising Stars final and a pair of enticing doubles matches as well. Here’s the run-down of what’s in store.
 Simona Halep (ROU #2) vs.  Flavia Pennetta (ITA #8)
Head-to-head: Pennetta Leads, 4-1
Key Stat: The top seed has won 22 of the 44 previous stagings of the WTA Finals.
Will Flavia Pennetta come up roses in her WTA farewell? Surely the 33-year-old Italian, who is the oldest Singapore participant this year, will be energized by the emotion and support she’ll feel in her first appearance at the WTA Finals, but let’s not forget that her first round robin opponent on Sunday is one of the WTA’s most loved—and most talented—players in Simona Halep (3-2, runner-up 2015).
Pennetta has dominated the matchup to date, winning four of five against the Romanian including a stirring 6-1, 6-3 victory at the U.S. Open semifinals this year. That was a contest that had Halep scratching her head. She later stated that she was inexplicably “flat” throughout the disappointing loss, and when asked by a reporter if a rain delay during the match had helped her at all against Pennetta, she deadpanned “Even the snow couldn't help me today.”
Joking aside, Halep will have to find a way to make a dent in Pennetta’s steady ground game by striking when the opportunity arises and by limiting her unforced errors. As for Pennetta, she’ll have to summon the magic of her U.S. Open run for one last hurrah without getting caught up in the emotions that are sure to be percolating below the surface. Pennetta did just enough to qualify for Singapore after the U.S. Open, going 3-2, but she’ll have to do more to defeat a higher-ranked Halep, who was a runner-up in her first WTA Finals appearance last season.
As far as first-day matchups go this is a cracker to get the ball rolling in Singapore—and it’s a tough one to call.
Pick: Halep in three tight sets
 Maria Sharapova (RUS #4) vs.  Agnieszka Radwanska (POL #6)
Head-to-head: Sharapova leads, 12-2
Key Stat: Sharapova has not completed a match since Wimbledon.
Finally, WTA Tennis fans will get a glimpse of a healthy Maria Sharapova, and what better place to do that than at one of the most prestigious, glamorous tournaments in women’s tennis? Tempered expectations are a big theme in the Sharapova camp as the Russian downplayed excitement about her return during media hour on Saturday by admitting that she’s not quite sure how she’ll play. "Look, it's a big step for me to be here and feel that I am healthy,” she said. “It will be a bigger step that I'll be able to compete in those three matches and finish them off healthy. That's my goal."
On Sunday Sharapova (18-8, 2004 champion) will face Agnieszka Radwanska (6-10), an opponent that she’s handled successfully 12 of 14 times since their first meeting in 2007. That’s the good news for Sharapova. The bad news is that Radwanska is playing lights-out tennis of late. The Pole has completely turned her season around since a sluggish start to the 2015 campaign and has gone 14-2 with two titles since the U.S. Open.
Radwanska’s losses to Sharapova haven’t all been blowouts. She has taken the Russian to three sets in five of her 12 career losses against her (including both of their previous WTA Finals meetings, in 2012 and 2014). Sharapova has found a way to get past Radwanska time and time again in the past, but if Radwanska pushes her to a decider on Sunday night in Singapore, how will Maria’s fitness hold?
Pick: Radwanska in three wild sets
Also on Tap: Doubles and Rising Stars
In Sunday’s first doubles battle at Singapore Bethanie Mattek-Sands and Lucie Safarova will meet Garbine Muguruza and Carla Suarez Navarro. This first-time meeting pits the two players (Muguruza, Safarova) who have qualified for Singapore in both singles and doubles against one of the two doubles teams to have won win multiple major titles in 2015.
The second doubles match will feature Timea Babos and Kristina Mladenovic vs. Andrea Hlavackova and Lucie Hradecka in another first-time meeting. Hlavackova and Hradecka are previous runner-ups (2012) at the WTA Finals, while Babos and Mladenovic are making their maiden appearance.timea babos
Caroline Garcia will face Japan’s Naomi Osaka in the final of the WTA Rising Stars Invitational. The pair of young guns met earlier in the week with Garcia coming out on top in three sets. Will Osaka take her revenge in the final?