FLUSHING MEADOWS, NY - Pictures of past U.S. Open champions stand affixed to flag polls around the Billy Jean King National Tennis Center. All-time greats like Jimmy Connors, Pete Sampras and John McEnroe are frozen in mid stroke, providing a glimpse of how drastically styles, equipment and even the game itself have changed.

Amid the tennis legends from the past 40 years of the Open era stands a picture of Marat Safin, who won the tournament in 2000. Since then, the Russian has struggled in Queens, failing to reach at least the quarterfinals since 2002. That string of disappointing finishes continued last night, when the lower-seeded Safin came out strong in the first set against No. 15 Tommy Robredo before falling, 6-4, 6-7 (4-7), 4-6, 0-6, Friday night.

A nearly two-hour rain delay near the end of the second set didn’t seem to face Safin as much as a tightly contested third set that went Robredo’s way. The Spaniard advanced to the third round and will face the winner of the Carlos Moya-Jo-Wilfried Tsonga matchup.

"Sometimes you have a good day, sometimes you have a bad day," Safin said. "Today I was struggling."

Robredo went up 5-4 in the second set and finally broke Safin’s serve, surging to a 2-1 lead in sets. At the outset, Safin assaulted the blue barriers behind the Louis Armstrong Stadium’s baseline with first serves as hard as 130 miles-per-hour. The 44th-ranked former champion’s service game gave him the first set and moved him ahead 5-4 in the second before rain forced both players into the dressing rooms.

"The rain was going on and off and I couldn't get into the game.,” Safin said. “I missed a few points in the tiebreak.”

Safin generated good pace on his backhand at the start by using his signature jump-before-hitting technique. The emotional Safin showed glimpses of the temper that got him in trouble in the first round, smashing his racket to the ground and drilling balls off the padding behind the baseline after poor shots or a failure to finish a volley.

"The third set was very close and the fourth set I lost it completely. It just slipped away and that's it," he said. "Too much frustration in the second and third set."

But after losing the third set, Safin fell apart in the fourth, winning just 10 points as Robredo won the set in just 24 minutes. His last two shots epitomized his brutal last set, crushing two easily hittable balls way wide down the right sideline. Instead of using his ferocious forehand to turn those opportunities into winners, Safin’s unforced errors ensured another early exit from the U.S. Open.

Safin will depart Flushing Meadows $2,000 poorer thanks to his outburst during a first-round match against American Vince Spadea. The International Tennis Federation announced the fine after Safin used a profanity at an official that went out over television over a controversial foot-fault call in the fourth set.