Stan Wawrinka recovered from a set behind to overcome Maxime Cressy and set up a second-round showdown with Andrey Rublev at the Madrid Open.

Three-time grand slam winner Wawrinka, who is the oldest player in the main draw, hit back in the Spanish capital to progress 6-7 (7-3) 6-3 7-6 (7-4).

The 38-year-old won 46 of 54 first-serve points and now has a couple of days to recover before facing fifth seed Rublev, who was handed a bye to the last 32.

Roberto Carballes Baena is also through after defeating David Goffin 6-4 6-4, with Alexander Zverev up next, while Alex Molcan saw off Wu Yibing 6-2 6-4.

There was a shock elsewhere on Wednesday as Diego Schwartzman was downed in straight sets by Hugo Grenier.

Casper Ruud clinched his 10th career ATP title with a straight-sets victory over Miomir Kecmanovic in Sunday's Estoril Open final, while Roberto Carballes Baena won the Grand Prix Hassan II.

Having enjoyed the best season of his career in 2022, Ruud was bidding for his first trophy success of 2023 in Portugal, and the world number five made a flying start to his clash with Kecmanovic.

Ruud wrapped up the opener in just 36 minutes, taking control with a huge forehand winner to break in just the third game.

The Norwegian navigated two three-set contests in order to reach the showpiece, and it looked like another of his matches may go the distance when Kecmanovic recovered to force a second-set tie-break.

However, a dipping backhand saw Ruud secure the second of two crucial mini breaks, and he took the first of his three championship points to cap a fine week with silverware, sealing a 6-2 7-6 (7-3) win.

Elsewhere, Carballes Baena won just his second career title, triumphing on the clay in Marrakesh where he beat Alexandre Muller 4-6 7-6 (7-3) 6-2.

France's Muller showed no signs of being overawed on his first final outing as he took the opener in impressive fashion, but Carballes Baena edged a tie-break in the second before dominating the decider.

Carballes Baena's triumph – recorded in just under three hours – gave him his first title since the 2018 Ecuador Open, which also came on his favoured clay surface.

Casper Ruud defeated Quentin Halys in a third-set tie-break to reach the final of the Estoril Open, where Miomir Kecmanovic awaits after defeating Marco Cecchinato.

The number one seed, competing in his first semi-final of the season, prevailed 6-4 3-6 7-6 (7-2) in Portugal to move within one match of a 10th singles title.

Ruud broke his opponent's serve in the opening game and saw out the first set, but Halys – competing in his first ATP Tour semi-final – hit back in the second to prolong the match.

Both men held as the contest went the distance, but Ruud's quality told as he raced 3-0 ahead in the deciding tie-break and did not look back as he set up a final with Kecmanovic.

World number 40 Kecmanovic needed a little over an hour to beat sixth seed Cecchinato, who had surprised Alejandro Davidovich Fokina in the previous round.

Kecmanovic, aiming to add to his only previous singles success in Kitzbuhel three years ago, held serve throughout to claim a 6-3 6-1 win over the 2018 French Open semi-finalist.

Elsewhere on Saturday, the final seeded player fell at the Grand Prix Hassan II as Dan Evans was defeated 2-6 6-4 6-2 by Roberto Carballes Baena.

Carballes Baena has now eliminated three seeded players and will face Alexandre Muller in Sunday's final after the Frenchman saw off Pavel Kotov in straight sets.

Muller edged a first-set tie-break and proved too strong in the second as he saw out a 7-6 (7-3) 7-5 victory in Marrakesh.

Casper Ruud is through to the final four of the Estoril Open after a routine 6-3 6-0 victory against defending champion Sebastian Baez on Friday.

The number one seed dominated his Argentine opponent from the moment the first set went to 3-3, winning nine-straight games from there to ease to victory.

Ruud did need to save four break points in the second game of the second set, but his ability to hold serve seemed to end any resistance that Baez could muster.

The Norwegian will face Frenchman Quentin Halys in the semi-finals after his own straight-sets triumph over Dominic Thiem

Halys reached his first ever ATP Tour semi after recording a 6-1 6-4 win over the former world number three in just one hour and 19 minutes.

The other semi-final will see Miomir Kecmanovic take on Marco Cecchinato after the latter stunned third seed Alejandro Davidovich Fokina in straight sets.

The world number 96 claimed a 7-5 7-6 (7-5) victory in the first meeting between the pair to set up a last-four clash with Kecmanovic, who saw off sixth seed Bernabe Zapata Miralles with a comfortable 7-5 6-2 win.

Elsewhere, Dan Evans is the only seed remaining in the Grand Prix Hassan II as he reached the semi-finals by cruising to a 6-3 7-5 triumph over world number 201 Andrea Vavassori in Marrakech.

Evans will face Roberto Carballes Baena next after the Spaniard toppled fourth seed Tallon Griekspoor 6-3 2-6 6-2.

Second seed Lorenzo Musetti was beaten by Alexandre Muller 6-3 1-6 6-4 in a topsy-turvy encounter, and the Frenchman will now face Pavel Kotov in the final four after the Russian defeated Christopher O'Connell in a thriller, 6-3 6-7 (6-8) 7-6 (7-3).

Fifth seed Casper Ruud secured his place in the last 16 of the Mallorca Championships with a straight sets win over Gilles Simon on Monday.

The 22-year-old claimed a 6-4 7-6 (7-4) victory to set up a meeting with Tennys Sandgren in the next round.

Following Ruud onto Centre Court, the American beat Spain's Jaume Munar 7-6 (7-3) 7-5 in just over two hours.

Sixth seed Karen Khachanov is also safely through, although he surrendered a set in beating French qualifier Lucas Pouille 7-6 (9-7) 3-6 6-4.

But Dusan Lajovic, seeded eighth, was not quite as fortunate.

Lajovic, ranked 41st in the world, was beaten 6-4 7-6 (7-2) by Slovakian qualifier Lukas Klein (ranked 256).

Feliciano Lopez came out on top of battle of Spaniards in the round of 32, beating Nicola Kuhn 6-1 7-6 (7-4).

Their compatriot Roberto Carballes Baena is in with a chance of joining them on Tuesday after seeing his clash with Sam Querrey paused due to light with both players having taken a set.

Elsewhere, Corentin Moutet beat Lloyd Harris to set up a meeting with top seed Daniil Medvedev, while Jiri Vesely and Stefano Travaglia also progressed.

Monday's other scheduled ATP event in Eastbourne saw play cancelled due to rain, with the scheduled match between Jo-Wilfried Tsonga and Egor Gerasimov pushed back as a result.

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