Tim Henman has been knocked out of the Toronto Masters by Wimbledon finalist David Nalbandian.

In a tight match, Henman failed to convert three match points in the second set and was made to pay as the Argentine came back from a set down to win 4-6 7-6 (9-7) 7-5.

Henman got off to a shaky start and was broken in the third game as Nalbandian appeared to settle quickly into his stride.

But Henman fought back to 3-4 before winning the remaining three games to take the first set 6-4.

The opening games of the second set went with serve. But as in the first Nalbandian broke the Henman serve in the third.

Henman was forced to attack from deep behind the baseline, making only the odd foray into the net.

And it took the fourth seed until the eighth game to level matters.

Henman then took 15 minutes to win the next service game as Nalbandian's ground strokes and passing shots continued to frustrate.

But Henman looked to be heading for victory as the set headed into a tie-break and he took a 6-3 lead.

However Nalbandian saved three match points before a superb backhand volley cross court gave him the tie-break 9-7.

In a nailbiting third set, both players comfortably held their serves early on.

But Henman was forced to save two break points in the sixth game to draw level at 3-3.

The Briton was always playing catch-up after that and at 5-6 down was broken when Nalbandian sent a fierce backhand shot flying past him to take the set and the match after two hours and 50 minutes.

Scorching heat

Yevgeny Kafelnikov was also a surprise loser, going out to Argentine Guillermo Canas.

Canas saw off the fifth seed 6-2 6-2 and will now face the number two seed Marat Safin of Russia in the next round.

Safin survived a scare in the third round before rallying to beat Chilean Marcelo Rios 3-6 6-3 7-6 (7-3).

Safin, the highest remaining seed after world number one Lleyton Hewitt's first-round exit, had to battle the scorching heat and a feisty Rios.

Rios broke his opponent to go 3-1 up in the deciding set, but Safin broke back in the seventh game and completed the win after a tie-break.

French pair Sebastien Grosjean and Fabrice Santoro both made comfortable passages into the next round with straight set wins over Radek Stepanek and Todd Martin respectively.

Third seed Tommy Haas beat Pete Sampras in three sets, while Andy Roddick easily defeated Stefan Koubek of Austria.

Thursday's results: