Australian Marinko Matosevic faces the toughest ask in tennis after winning his first match on clay in almost a year to open with a 7-5, 6-3 success over Fernando Verdasco at the Monte Carlo Masters on Tuesday.
But the number 54 won't have time to celebrate an upset of Spain's former ace.
Instead, he will become just the first obstacle placed in the path of Rafael Nadal as the king of clay begins a bid for an unprecedented ninth straight championship at the Country Club overlooking the Mediterranean.
Matosevic sprang a surprise on Verdasco, the one-time clay powerhouse and 2010 runner-up here to Nadal, going through to the second round in a struggle as his Spanish opponent fought back at the end in the one-hour, 51-minute contest.
Matosevic saved nine of the dozen break points he faced while breaking the 31st-ranked Verdasco on five occasions.
The Australian last won a clay match in the first round of French Open qualifying last May after earning his last ATP win on the surface in Munich a few weeks earlier.
Nadal takes a fearsome 42-match win streak in Monte Carlo into his second-round opener after a bye. The 11-time grand slam champion last lost in the principality as a teenager in 2003 to Guillermo Coria.
Top seed Novak Djokovic was preparing to decide if he will be fit enough on his rolled ankle to make his start on Wednesday, when Nadal and Matosevic also clash.
Djokovic has been putting in training and tests on his right ankle and promised to decide his immediate future later in the day. The world number one would make a start against Russian Mikhail Youzhny, who stands a respectable 3-4 in their career series.
In other first-round matches on a perfect, sunny day, Swiss 13th seed Stanislas Wawrinka beat Denis Istomin of Uzbekistan 6-3, 7-5 while Spaniard Albert Ramos defeated Radek Stepanek 6-3, 6-3 as the 34-year-old Czech played his first ATP match since the Australian Open after undergoing surgery to ease pressure on a nerve.
In the second round, Bulgarian Grigor Dimitrov upset eighth seed Janko Tipsarevic 7-6 (7/3), 6-1.