The 15th seed and birthday boy Denis Shapovalov will have enough time to prepare for the ATP 500 Barcelona event, suffering the first-round Monte Carlo loss to Jan-Lennard Struff 5-7, 6-3, 6-1 in an hour and 58 minutes. Denis prevailed against Jan-Lennard in Tokyo last year but stood no chance today after winning the opening set, dropping ten of the last 11 games to propel the German into the second round.
The Canadian hit 22 winners but also 51 unforced errors, spraying them from both wings and adding ten double faults to his poor tally, losing the edge to Struff in the shortest rallies and suffering the eighth loss of the season.
Both players saved three break points in the opening games of the match and traded breaks in games five and six to stay neck and neck. Shapovalov repelled three break points in game seven and had the set in his hands at 5-4 when Struff played against three set points, wasting them all before finding the desired break at 6-5 to grab the opener in just under an hour.
Trailing 3-2 in set number two, Jan-Lennard shifted into a higher gear to claim the next four games and the set 6-3, earning breaks in games seven and nine and building momentum before the decider. There, the youngster failed to make an impression on the return, as many times before in the matches where he was on the negative side of the scoreboard, losing serve in games two and six to send Jan-Lennard in front and allowing him to cross the finish line with a hold at 5-1.
The 10th seed Daniil Medvedev matched Roger Federer's 18 wins in 2019, toppling Joao Sousa 6-1, 6-1 in 54 minutes after one of the best performances on the slowest surface so far in a career. The Russian had 16 winners and 11 unforced errors, controlling the pace in the rallies regardless of their length and never facing a break point to mount the pressure on the other side of the net.
Sousa was nowhere near that level, dropping 60% of the points behind the initial shot and getting broken five times from eight chances offered to Daniil. The youngster kicked off the encounter with a hold at love after a service winner, breaking the Portuguese in the next game when Joao netted a forehand.
Another terrible groundstroke sent Sousa 5-1 down and Daniil sealed the opener with an ace a few minutes later for a 6-1 after 28 minutes. There was only one player on the court in set number two, with Medvedev taking 24 out of the final 33 points to march towards the finish line, delivering three straight breaks and six games overall to book the place in the last 32.
Philipp Kohlschreiber will have a chance to play against Novak Djokovic once again at Masters 1000 events in 2019, beating Taro Daniel 6-1, 6-3 in 67 minutes, losing just nine points in eight service games and stealing almost half of the return points to secure four breaks from eight chances.
Finding the range right from the start, Philipp won seven straight games and cemented the triumph with a better performance at 3-3 in set number two to secure the place in the next round. Roberto Bautista Agut is Rafael; Nadal's first rival, defeating John Millman 3-6, 6-1, 6-1 in an hour and 51 minutes after fending off six out of eight break points.
Millman was off to a great start but he couldn't maintain that form, taking only 12 points on the return in sets two and three to push the Spaniard into the second round. The 11th seed Marco Cecchinato stayed on the court for just 19 minutes, scoring a win when Damir Dzumhur retired while trailing 4-0 and saving energy for the next encounters.