The world No.33 crashed out of the BNP Paribas Open at Indian Wells with a 6-4 6-4 loss to Philip Kohlschreiber in the second round (his first match of the tournament) on Monday.
Action continues on the hard courts of Indian Wells tomorrow.
Monfils has a 13-2 career record against Kohlschreiber.
He made no mistake on his second chance, however, firing a sideline-skimming forehand to seal the milestone win on his first match point.
"It's a very special win today", Kohlschreiber said after the match. 2 Rafael Nadal in the 2012 Halle quarter-finals. "I need to do what I want, and what I want is to play the tournaments I want to play". I had two good wins.
The 22-year-old will next face Canadian teenager Denis Shapovalov, who continued his run of dominant serving without being broken on his way to an impressive 6-4 6-2 win over 10th seeded Croat Marin Cilic.
While Federer and Nadal have voted against having Chris Kermode as ATP Chairman, Player's Council President Djokovic has backed Kermode.
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It did not matter in the end, though, as Rennes failed to find a way through at the other end. Arsenal are in the Europa League quarter-finals after seeing off Rennes .
After losing one point, the 15-time Grand Slam champion flung his racket at an advertising board in anger. "It feels great, it means that I'm pretty old and have been on the tour for a long time", he said at the time.
Kohlschreiber's only prior win over Djokovic came back in 2009, a three-set victory at Roland Garros. The other two? Boris Becker (713) and Tommy Haas (569), the current BNP Paribas Open Tournament Director. "He's been close to the Top 10 for many years and has beaten many top players. I did a lot of things well", said Nadal, adding that despite his lopsided record over Schwartzman he considered the Argentine a formidable opponent, citing tough matches against him at the Australian Open and Roland Garros.
He came out with a crisp, confident style, breaking Djokovic in the seventh game and closing out the opening set with a service victor. "I'm not at my highest level, but slowly building, and hopefully I'll be able to peak in Miami".
"I really wasn't focusing so much on her".
But should more fame come with more success, Kohlschreiber would be fine with that, too. I was able to mix up my game, cover my serve, be risky on the return - maybe take some rhythm away from Stan.
"Miami is the next tournament singles-wise for me, [but] I'm going to try to go all the way here in doubles".
He said: "Whatever the problems were with Djokovic, whether he is less than 100 per-cent medically or whether the off-court politics have got to him - who knows, Kohlschreiber has beaten him".