( CNN ) -- Canada 's rising star Milos Raonic broke more new ground when he reached the first clay quarterfinal of his short top-level career in Portugal on Thursday . The 20-year-old , seeded fifth at the Estoril Open , set up a clash with French No . 4 Gilles Simon after beating local wild-card entry Joao Sousa 6-3 6-3 . Raonic , the second-youngest player in the top-100 , is the highest-ranked Canadian in the history of the ATP Tour at 27th . He has leapt up from a year-starting 156th following his first title at the San Jose hard-court event and then a losing final in Memphis earlier this year , also reaching the fourth round of the Australian Open . Is Nadal 's clay domination good for tennis ? Raonic lost in the last 16 in the European season 's opening clay events at Monte Carlo and Barcelona this month , which both had bigger entry fields , as he attempts to adapt his big-serving game to the more subtle surface . `` He 's the player with some of the best for this season , '' world No . 22 Simon told AFP of a player who has the third-fastest serve on record . `` He 's playing well but he does n't have that much experience on clay . `` I think it might be better to play him now instead of for the first time when he may be in the top 15 . '' Simon beat Argentina 's Carlos Berlocq 6-2 6-1 in his second-round match . The winner of his clash with Raonic will take on either second seed Fernando Verdasco or South Africa 's big-serving Kevin Anderson in the semifinals . Verdasco has dropped from ninth to 15th in the rankings after a run of early exits , but he rebounded to beat another Portuguese wild-card , Frederico Gil , 6-1 7-6 ( 7-5 ) . Seventh seed Anderson defeated Victor Hanescu 6-4 6-2 , avenging his defeat by the Romanian in the second round in Barcelona . Djokovic eases past Ungur in Belgrade . In Belgrade , second seed Viktor Troicki crashed out in second round of his home Serbia Open . The world No . 16 , who helped Serbia win last year 's Davis Cup final , lost 6-2 6-3 to 52nd-ranked Spaniard Marcel Granollers . Granollers will next face unseeded Italian Filippo Volandri , who beat Ukraine 's Illya Marchenko 6-3 1-6 6-3 . Third seed Guillermo Garcia-Lopez also crashed out against India 's Somdev Devvarman . Devvarman , ranked 71st , had lost to the Spaniard in Houston on clay this month but triumphed 7-6 ( 8-6 ) 2-6 7-6 ( 10-8 ) . He will next play seventh seed Janka Tipsarevic after the Serbian beat Russia-born German Mischa Zverev 6-2 6-0 . In Munich , third seed Marin Cilic , No . 5 Florian Mayer and fellow German Philipp Kohlschreiber reached the quarterfinals of the BMW Open on Thursday . Croatia 's Cilic will take on Russian seventh seed Nikolay Davydenko following his 6-3 7-6 ( 9-7 ) win over Argentina 's Horacio Zeballos . Mayer beat Russia 's Teimuraz Gabashvili 6-4 7-6 ( 7-1 ) to set up a clash with young Bulgarian Grigo Dimitrov , while eighth seed Kohlschreiber faces Czech Radek Stepanek after eliminating compatriot Denis Gremelmayr 6-3 6-3 . In the semifinals of the Barcelona Women 's Open , Italian fifth seed Sara Errani will play Lucie Hradecka of the Czech Republic . Errani won 6-3 6-2 against compatriot Alberta Brianti , who won the Fes Grand Prix in Morocco last weekend . Another Italian reached the last four after sixth seed Roberta Vinci beat France 's Virginie Razzano 6-4 6-1 to set up a clash with Slovenia 's Polona Hercog or Spain 's Laura Pous-Tio . The top three seeds of the women 's event in Estoril all lost in the quarterfinals on Thursday . Top-ranked Alisa Kleybanova of Russia lost 6-4 6-2 to Germany 's Kristina Barrois , who came back from 4-1 down in the opening set . The 19-year-old will next face Sweden 's 80th-ranked Johanna Larsson , who beat Russia 's Alla Kudryavtseva 6-2 7-5 . Austrian second seed Jarmila Gajdosova also tumbled out , losing 5-7 6-4 6-2 to Romania 's Monica Niculescu . Niculescu will take on Spain 's Anabel Medina Garrigues , who beat Czech third seed Klara Zakopalova 6-3 7-5 .
Fifth seed Milos Raonic sets up quarterfinal against French No . 4 Gilles Simon . Canadian , ranked 27th , is the second-youngest player currently in the world 's top-100 . TL;DR Top three players eliminated in quarterfinals of women 's event in Portugal .