MONACO — Three-time Grand Slam winners Andy Murray and Stan Wawrinka had contrasting fortunes in the first round of the clay-court Monte Carlo Masters on Monday.

Former champion Wawrinka rallied to win 5-7, 6-3, 6-4 against Dutchman Tallon Griekspoor, sealing victory on his sixth match point.

The 38-year-old Swiss, who won here in 2014, next plays American Taylor Fritz.

Murray lost 6-1, 6-3 to 14th-seeded Alex De Minaur. The 35-year-old Murray, who has a metal hip, struggled against the Australian's court speed in their first meeting on clay, losing the first set in 34 minutes after dropping serve a third time.

De Minaur served out the match on his first match point when Murray's backhand hit the net, and he improved to 3-0 against the British player. De Minaur plays Jan-Lennard Struff next.

Former Wimbledon finalist Matteo Berrettini of Italy won 6-4, 6-2 against unseeded American Maxime Cressy, who served 14 double-faults.

Berrettini, who has dropped to 22nd in the rankings, next faces Francisco Cerundolo. The unseeded Argentine won 90% of his first-serve points in a 6-3, 6-4 win against 11th-seeded Briton Cameron Norrie.

Dominic Thiem had six aces and did not face a break point as he beat French veteran Richard Gasquet 6-1, 6-4.

Thiem has reached the final at every Grand Slam except Wimbledon, twice losing in the French Open final and once at the Australian Open before finally winning at the US Open in 2020.

The 29-year-old Austrian reached a career-high No. 3 in the rankings that year, but his form dropped following a right wrist injury and he's now 106th.

Thiem announced on Saturday that he was parting ways with coach Nicolas Massu after four years together. Thiem next plays Paris Masters winner Holger Rune of Denmark, who is seeded sixth.

Diego Schwartzman won 6-4, 6-2 against Belgian David Goffin and next faces seventh-seeded Italian Jannik Sinner.

Briton Jack Draper beat Sebastian Baez 6-3, 7-5 to set up a match against 10th-seeded Hubert Hurkacz.

In Tuesday's second-round action, top-ranked Novak Djokovic of Serbia and two-time defending champion Stefanos Tsitsipas of Greece start their bids to win the tournament for the third time.

Djokovic faces Russian qualifier Ivan Gakhov while Tsitsipas takes on Frenchman Benjamin Bonzi.

No. 13 Alexander Zverev, a French Open semifinalist the last two years, faces Alexander Bublik — who said during last year's tournament how much he dislikes clay.

Record 11-time Monte Carlo champion Rafael Nadal and second-ranked Carlos Alcaraz pulled out of the tournament.

AP