- Diego Schwartzman pulled off the match of his career Saturday at the Italian Open, beating Rafael Nadal
- Denis Shapovalov is looking for his second career Masters 1000 final – and his first foray into the top ten of the ATP rankings
- Novak Djokovic remains the favorite to win in Rome. Can anyone stop him?
Continuing the trend from the US Open, there are new faces in the final stages of the Italian Open, a Masters 1000-level tournament that’s just below the Grand Slam events.
The familiar face is Novak Djokovic, but joining him are world No. 34 Casper Ruud, No. 14 Denis Shapovalov, and No. 15 Diego Schwartzman.
The semifinals are slated for Sunday, Sep. 20th, with a rare Monday final on tap for the 21st. Bet365 has Djokovic heavily favored over Ruud – as expected – while Schwartzman is the slight chalk against Shapovalov.
Italian Open Men’s Singles Semifinals Odds
|Player||Moneyline Odds at DraftKings|
| Novak Djokovic (SRB)||-590|
|Casper Ruud (NOR)||+450|
| Diego Schwartzman (ARG)||-143|
| Denis Shapovalov (CAN)||+120|
All odds taken Sept. 19
 Diego Schwartzman vs.  Denis Shapovalov
On Saturday, Schwartzman shocked clay-court king Rafael Nadal 6-2, 7-5 in the quarterfinals.
He won as many sets (two) as he had in their first nine meetings combined on a night he played his best and Nadal … didn’t.
The Argentine’s problem now is that he can’t afford to bask in the glory of his career-best victory. He remains very much in in the running to win a prestigious title.
In the semifinals he faces a friend, Shapovalov, against whom he practiced for several weeks earlier this summer in the Bahamas as both were preparing to return to play.
The two pals, seven years apart in age, had never met before.
On the plus side for Schwartzman, he will be facing another left-hander in Shapovalov one day after topping lefty Nadal.
On the minus side, Shapovalov is nothing like Nadal.
Only Schwartzman Can Stop Shapo’s Top-10 Promotion
Between singles and doubles, his quarterfinal at the US Open and now his semifinal in Rome, Shapovalov has been a busy man.
All the tennis has clearly been good for him. Schwartzman said Saturday night that, with Shapovalov, you could always count on a stretch of a few games when he’d go off form and give you some errors.
But at the moment, the 21-year-old Canadian is the model of consistency and confidence.
This is the fifth Masters 1000 semifinal for Shapovalov, who also reached the semis in Canada (2017), Madrid (2018), Miami (2019), and Paris-Bercy (2019).
— Tennis TV (@TennisTV) September 19, 2020
If Shapovalov beats Schwartzman, he jumps into the top ten for the first time in his career. Even if he loses, he can still make it if Schwartzman loses in Monday’s final.
He will likely play better than Nadal did in defeat Saturday. It would be hard not to; Nadal’s first-serve percentage was below 50 percent, and he won fewer than 50 percent of points on both his first and second serves.
Pick: Shapovalov (+120) in straight sets
 Novak Djokovic vs. Casper Ruud
In the wake of Djokovic’s disqualification at the US Open for hitting a line umpire with an errant ball, he had a brief period of self-reflection and got back out there this week in Rome.
Overall, his tournament has been … okay, certainly nothing special by his standards. And yet, he’s two matches away from the title.
It took Djokovic three sets to dispatch German qualifier Dominik Koepfer in the quarterfinals Saturday. It was a bit of a roller coaster, and Djokovic had his moments.
Ultimately, he survived and advanced, as he almost always does, and now he faces an unseeded player in Casper Ruud. The Norwegian is also outside the top 30, but is superior to Koepfer.
Ruud had a career match of his own Thursday, coming back to from a set down to upset No. 4 seed and Rome native Matteo Berrettini in a third-set tiebreak.
The inexperienced 21-year-old, who looked exhausted at the end of the win over Berrettini, may struggle to get his level back up to what will be needed to defeat Djokovic. But, to coin a phrase, he has nothing to lose and everything to gain.
This, too, will be a first-ever meeting. Take the match to go three sets at Bet365 (+225).
Pick: Djokovic (-590) in three sets
Let's have fun and keep it civil.