Marat Safin was the big casualty on the second day of the Madrid Masters as he crashed out at the hands of Agustin Calleri.

Safin currently lies third in the Champions Race and looks safe for a place in the end-of-season Masters Cup, but a good run in Madrid would have made his place certain.

He lost in two tie-break sets to Argentine Calleri, losing the first 8-6 and the second 7-5.

The Russian took the defeat in typically moody fashion in a match which did not finish until the early hours of the morning.

Calleri's reward is a match-up with either Thomas Johansson or fellow Swede Magnus Norman in the next round.

Paradorn Srichaphan set up a second-round meeting with Tim Henman after he sent Gustavo Kuerten crashing out of the Madrid Masters.

Henman, still suffering the effects of a shoulder injury, has not played since defeating the Thai number one to clinch Britain's qualification for the Davis Cup World Group.

"I've played Tim four times already and I haven't won one yet," said Srichaphan.

"But I'm going to try my best because he's a great player.

"The wins just keep on coming and I feel confident enough to go out and take on anyone."

Srichaphan, the newly-crowned Asian champion and winner of his first career title at Long Island this summer, took control early against Kuerten.

Moya and Grosjean advance

The 23-year-old Thai broke the former world number one's serve once in each set and is now knocking on the door of the world's top 25 after a breakthrough year.

Henman's performance in Madrid could be crucial to his hopes of qualifying for the Masters Cup in Shanghai.

He currently lies fifth in the Champions Race and needs to keep his place in the top seven if he is to make the trip to the prestigious event.

In second-round matches on Tuesday, eighth seed Carlos Moya came from behind to defeat big-hitting Chilean Fernando Gonzalez 2-6 7-6 7-6.

Moya had to save a match point in the second set before progressing after two tough tie-breaks.

While the Spaniard needed all his experience to see off one of the game's brightest prospects, Sebastien Grosjean joined him in the third round with rather less drama.

The Frenchman was leading Xavier Malisse 5-1 on number when the Belgian was forced to retire because of injury.