A blockbuster showdown more worthy to be played much later in the week will take place on Thursday between Dominic Theim and Novak Djokovic. A quarterfinal spot will also be on the line when Grigor Dimitrov goes up against Philipp Kohlschreiber.
(9) Novak Djokovic vs. (5) Dominic Thiem
Thiem and Djokovic will be squaring off for the seventh time in their careers when they clash in round three of the Monte-Carlo Rolex Masters on Thursday. Djokovic is dominating the head-to-head series 5-1, but Thiem cruised through their most recent encounter 7-6(5), 6-3, 6-0 in the quarterfinals of last year’s French Open. Due mainly to injury, Djokovic has not been the same since. The 30-year-old Serb did not play after Wimbledon in 2017 and he is just 5-3 this season, which explains his plunge to No. 13 in the rankings. On the bright side, Djokovic has raised his level in Monte-Carlo to the tune of straight-set victories over Dusan Lajovic and Borna Coric.

Also one of Rafael Nadal’s top clay-court challengers when healthy, Thiem sustained a knee injury at the Indian Wells Masters and skipped Miami. Now on his favorite surface, the seventh-ranked Austrian survived a stern test from Andrey Rublev and saved one match point before prevailing 5-7, 7-5, 7-5 on Tuesday. Although this is an improved Djokovic from what was on display at the last two Masters 1000 events, he needed 10 match points and a total of two hours and 15 minutes to get past Coric on Wednesday. The former world No. 1 is nowhere near as match-tough as he is at his best, and a date with one of the best clay-courters in the world this early in the spring swing may be too difficult.
Pick: Thiem in 3
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(4) Grigor Dimitrov vs. Philipp Kohlschreiber
Dimitrov and Kohlschreiber will be going head-to-head for the second time in their careers on Thursday. Their only previous meeting also came during the clay-court swing, as Dimitrov got the job done 7-6(7), 6-4 last year in Madrid. The fifth-ranked Bulgarian wrapped up his 2017 campaign with a triumph at the Nitto ATP Finals, but he is once again flying under the radar with a modest 12-6 record this season. A horrendous 1-4 in his last five matches prior to arriving in Monte-Carlo, Dimitrov overcame qualifier Pierre-Hugues Herbert 3-6, 6-2, 6-4 on Tuesday.
Kohlschreiber has been busy in the early stages of the clay-court season, and that is an understatement. In Germany’s road Davis Cup tie against Spain, he got blown out by Nadal before losing the decisive fifth rubber against David Ferrer 7-6(1), 3-6, 7-6(4), 4-6, 7-5. The world No. 40 still played the very next week and that decision proved to be a poor one, as he was upset by Lamine Ouahab in the Marrakech opening round. If nothing else that allowed Kohlschreiber to rest, and he undoubtedly used the time off to his benefit prior to Monte-Carlo victories over Tennys Sandrgen (6-2, 6-2) and Albert Ramos-Vinolas (6-4, 6-2). This one could go either way, but the underdog’s mental scarring from having come out on the wrong end of so many competitive matches may once again be the difference on Thursday.
Pick: Dimitrov in 3
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