Safin, who has been out of the top 10 since January 2006, has a propensity to throw matches away and Monday's encounter with Monaco was no exception.
The Russian, who lies 31st in the ATP rankings, had already lost the first set and smashed a racket on the court when the clock ticked past the 20-minute mark.
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He then served four double faults in the opening game of the second set as Monaco opened a 2-0 lead. The Russian broke back to level to 2-2 but lost the tiebreak 7-4 and stumbled out of a tournament he has won three times.
"I had my opportunities but unfortunately it was a bit too late already because the guy started to play well and started to feel much more comfortable on the court," said Safin.
"I didn't take my chances, that's why the score is 6-0 7-6."
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