When the draw was revealed for the Monte Carlo Open it's a fair bet Jordan Thompson decided to give the Principality's famous casino a miss for the week, as his luck clearly wasn't in.
His second round pairing was with Stefanos Tsitsipas, who had a 20-3 record on the red clay of Monaco and had won three of the last four events.
But Thompson is not one to be fazed by a bad draw, and he gave the Greek a fright before losing 4-6 6-4 6-2 in just over two hours.
But there was an Australian success with Alexei Popyrin gaining a impressive first round comeback win over world No.20 Ugo Humbert.
Eighth seed Alex de Minaur, the other Australian in the event, makes his bow Wednesday (local time) against Tomas Machac. De Minaur had a first round bye.
Thompson took the first set in his match, during which he dropped only four points on serve.
But Tsitsipas has been in the world's top 15 for six years because he can solve problems, and he resolved this one, stepping inside the baseline to return.
"I tried to work around my serve, I felt like these were the moments that were tricky at the start of the match," said Tsitsipas.
"Once that felt more consistent, I tried to focus on my return. Trying to return from far back didn't seem to work much. I have had success returning far back on clay courts, but today it didn't do the job, so I had to rely on closer returns, and it seemed to work well."
The shock of the day was top seed Alexander Zverev losing 2-6 6-3 7-5 to unseeded former Wimbledon finalist Matteo Berrettini.
Zverev, the French Open runner-up last year, was broken in the seventh game of the deciding set but broke back with Berrettini serving for the match at 5-4.
After an intense 11th game — featuring a 48-stroke rally at deuce won by Berrettini — the Italian earned another break of serve and another chance to serve out the match. This time he took it.
Berrettini, who has won 17 of his past 18 matches on clay, next faces either Jiri Lehecka or 13th-seeded compatriot Lorenzo Musetti.
in the other second round match Rising Brit Jack Draper made a superb start to his claycourt season with a comprehensive 6-1 6-1 victory over Marcos Giron
Popyrin beat Ugo Humbert 3-6 7-6 (7-2) 6-4 in a lengthy two-hour, 50-minute battle.
The first set was not as one-sided as the score suggests. Broken in the fourth game Popyrin had a break point to get back on serve in the ninth but failed to take it.
In the second set Popyrin was 30-40 down in the 11th game and 40-15 up in the 12th, but in both cases the break was averted. The world No.27 dominated the tie-break, racing to a 6-0 lead against a player ranked No.20, then broke in the ninth game of the decider before serving out.
The Australian now meets Frances Tiafoe who beat Miomir Kecmanovic 6-2 5-7 7-6 (7-5).
Among other remaining first-round matches, Holger Rune of Denmark was trailing 6-2 3-0 against Nuno Borges when he retired after feeling unwell.
"I clearly saw that he wasn't feeling great," Borges said.
No. 15 seed Grigor Dimitrov beat Nicolas Jarry 6-3 6-4 on his seventh match point and next meets local wild card entry Valentin Vacherot.
