More often than not, Dimitrov had the answers in his win over Cuevas

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MELBOURNE—Grigor Dimitrov is eminently likeable. Kind and devoted, earnest in the manner of a prep school lad gearing up for the SAT, this 27-year-old man from Bulgaria has many qualities that have made him a fine ambassador for his sport. Watch Dimitrov play his best tennis and you will witness a pleasing mix of movement, shot-making and, most captivating for many, a fluid, one-handed backhand. Those assets have long-promised to earn him a permanent seat at tennis’ big boy table—that is, within frequent striking distance of Novak Djokovic, Rafael Nadal and Roger Federer.

But they haven’t. A year ago, Dimitrov arrived here ranked third in the world. Toppled in the quarters by 49th-ranked Kyle Edmund, Dimitrov only won two more matches at the next three majors and is now ranked 21st. And so it was tonight that he labored on Court Three to beat 94th-ranked Pablo Cuevas 6-3, 6-7 (5), 6-3, 7-5.

Tearing his way through the first set, 6-3, in 29 minutes, all seemed on course for Dimitrov. Cuevas served in the second at 5-5, 15-40—at which point Cuevas threw down three straight aces.

One could only wonder what the latest addition to Dimitrov’s coaching staff made of seeing his charge aced three times in a row. Andre Agassi, owner of one of the finest service returns in tennis history, had joined the Dimitrov fold last fall. Agassi had also seen his share of bold and versatile players armed with one-handers, both in the form of his greatest rival, Pete Sampras and, later, Federer.

But while Sampras and Federer managed the court like field marshals commanding legions into battle, there is a hesitancy lurking within Dimitrov that so often turns the theoretically routine into the surprisingly epic. Such a threat pervaded this evening. The second-set tiebreaker revealed much. For all Dimitrov’s gifts, Cuevas was the one who controlled more of the court space.

Only in the third was Dimitrov able to vault ahead, his campaign aided by three double-faults from Cuevas at 1-2. Serving at 5-3, a trio of winners helped Dimitrov close out the set at love.

But once again, the Dimitrov Dilemma. He jumped off to a 15-40 lead on Cuevas’ serve in the opening game of the fourth. This is precisely the moment when Sampras and Federer had snapped open their matches. Go ask Andre. Alas, this was precisely the stage where Dimitrov stumbled in the tennis course that has long frustrated him: Court Management. Staring at the abyss—but not pushed into it by Dimitrov—Cuevas held and began to feel increasingly liberated.

My message to Dimitrov is the same one I sent to Tommy Haas years ago: You are beautiful. Your one-handed backhand is beautiful. Get over it. Get under it. Most of all, get in on it. Standing back on the baseline admiring that pretty shot’s occasional precision is the equivalent of combing your hair when what you really should do is pick up the phone and call that girl. Get in there, buddy. And please make it a call, not a text.

When a dose of opportunism and forward movement would have put Dimitrov behind the wheel, instead, through much of the fourth, he occupied the passenger’s seat. There came a moment when Dimitrov escaped from a 2-3, love-30 deficit.

Credit to Cuevas. No one has ever watched him with the spirit of tennis rapture. But say this: You must drive the stake through his heart—and face a barrage of crosscourt drives.

At 5-all, though, Dimitrov at last found what I’ll call the Shot Shank Redemption. Cuevas served at 40-love. A tiebreaker appeared imminent. But Dimitrov bullied Cuevas around the court just well enough to earn a break point. Mid-rally, he shanked it wide. But two points later, Cuevas down break point again, it was his turn to spray one, flagging a forehand long. After two hours and 45 minutes, Dimitrov had earned the chance to serve out the match. Here, he grabbed the wheel convincingly, closing it out at 15.

Dimitrov won a sparkling 21-of-26 points at the net, including nine of 10 in the last two sets. With that kind of success rate, why not try it more? Though tonight Dimitrov had just enough answers, when it comes to his prospects, it’s impossible not to continue asking questions.

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