Each day during the Australian Open, we'll select three of the most intriguing matches on the schedule and offer our predictions.

Alexandr Dolgopolov [13] vs. Bernard Tomic (Rod Laver Arena, first night match)
Head-to-Head: Dolgopolov leads 3-0

An appealing match between two unconventional characters with such flair for finesse they sometimes look intent on rearranging strands of felt from the ball, with their penchant for playing drop shots and soft slices—only to haul off and hammer flat drives. Dolgopolov grew up looking up to Marcelo Rios, and the Ukranian's capacity to create angles, amp up the pace of his shots, and disguise direction from seemingly the same swing is reminiscent of the 1998 Australian Open finalist.

Court coverage could be a key to this match: Dolgopolov, likely one of the 10 fastest men in tennis, is so light on his feet it sounds like he’s playing in slippers. The long, lanky Tomic is not nearly as quick around the court, but compensates with an expansive wing span and an audacious ability to control touch shots struck on the run. Tomic slid several slice backhands down the line while on the move during his comeback from a two-set hole against Fernando Verdasco in the first round, and tormented Sam Querrey at times with the drop shot-lob combination. Look for Tomic to hit behind Dolgopolov to try to use his speed against him.

The 13th-ranked Ukranian owns a 3-0 edge over Tomic, with all three wins coming on hard courts. He was runner-up to Andy Murray in Brisbane and is making a Top 10 push. Based on ranking, recent results, past history, and the fact he is defending quarterfinal points in Melbourne, you have to favor Dolgo to win this match. But sometimes when you visit the shotmaker’s circus you leave logic at home. I definitely do not underestimate Dolgopolov—remember, he beat Jo-Wilfried Tsonga and Robin Soderling last year, and gave Andy Murray a four-set fight in the quarterfinals—and though he was pushed to five sets by 198th-ranked Greg Jones in the first round and 98th-ranked Tobias Kamke in the second, Dolgopolov has won four straight five-setters in Melbourne. Despite concerns that Dolgopolov’s speed will shrink the court and coax Tomic into errors, I’ll take the risk and ride with street racer Tomic to continue his winning run.

The Pick: Tomic in 5.

Nicolas Almagro [10] vs. Stanislas Wawrinka [21] (Court 2, third match)
Head-to-Head: Wawrinka leads 3-1

A celebration of the wonders of the one-handed backhand pits two sturdy 26-year-olds with muscular games who can crack one-handers for winners from virtually any spot on the court.

Almagro has been hanging in or around the Top 10 for the past year, won three titles in five finals last season, and has reached the round of 16 in Melbourne two years in a row. With the exception of two Roland Garros quarterfinal appearances, Almagro’s Grand Slam history is one of unfulfilled potential: He’s exited in the opening round in three of his last six majors. He lacks the explosive speed Top 10 players possess, but Almagro is a power player capable of pounding shots down the line off both wings. Beneath the burden of major stress, an ornery Almagro has a tendency to berate himself, blast balls at warp speed, and sometimes looks on the edge of erupting into the tennis equivalent of road rage. But the 10th seeded Spaniard's ferocious five-set comeback over Grigor Dimitrov in round two— his first five-set win since he beat Igor Andreev in the second round last January—could inspire him here.

Wawrinka took charge in the fourth set of his second-round win over Marcos Baghdatis, hitting 10 winners to one for the former Oz finalist. The Swiss is most dangerous on hard courts when he steps closer to the baseline and applies pressure by taking the ball earlier and mixing in some well-timed runs to net. (He won 20 of 31 net points vs. Baghdatis.) Both players love to take the big strike, and neither is a speed merchant, so we should see a slew of winners in this match. Wawrinka leads their head to head, has had more success in hard-court majors, and played with confidence in key stages versus Baghdatis—and I give him the edge here.

The Pick: Wawrinka in 4.

Jelena Jankovic [13] vs. Christina McHale (Margaret Court Arena, fourth match)
Head-to-Head: Jankovic leads 1-0

The lone teenager still standing in the top half of the draw, McHale is through to the third round of her second straight major. Some have compared her to another former American teenage hope, Melanie Oudin, but I think the 42nd-ranked McHale has a higher upside. Both favor the forehand, but McHale hits hers with more topspin, enabling her to create sharper angles and play effectively on several surfaces. McHale has scored four of her five career Top 20 wins in the last year, including an upset of ninth-ranked Marion Bartoli at the U.S. Open last summer, and can surprise with a sneaky-quick first serve and a scrappy skill for extending rallies.

Former world No. 1 Jankovic has been tagged as tennis’ drama queen for her stressed-out soliloquies directed at her box and the various aches, pains, and injury time-outs that can surface when she’s engaged in tight matches. For a measure of Jankovic’s confidence, watch her feet closely. When Jankovic is actively moving forward and setting up for shots quickly, she makes better use of her strengths—her court coverage, anticipation, athleticism, and one of the best two-handed backhands in women's tennis—to play a bit more ambitious. When she's not confident, she becomes content to play balls back down the middle, retreat into a defensive shell, and allow opponents to drag her around the court..

Though she sometimes over-plays the two-hander down the line—a potentially risky play against the McHale forehand—I think Jankovic is the better athlete and has more shots, if she chooses to use them. While she can get flaky and cranky if she’s missing, the Serb is a rhythm player who will gain confidence playing the longer rallies she should see in this match. Jankovic spent the off-season training in Las Vegas, and says she’s committed to returning to the Top 10. I believe she will play higher-percentage tennis and make McHale do something special to beat her. This is an opportunity match: The winner could face world No. 1 Caroline Wozniacki next, and while an upset wouldn't shock, I see Jankovic winning.

The Pick: Jankovic in 3.