Daniil Medvedev entered the Rolex Monte-Carlo Masters with two victories from 11 tour-level matches on clay, but that didn’t stop the Russian from claiming the biggest victory of his career on Friday.

The 23-year-old stunned Novak Djokovic 6-3, 4-6, 6-2, breaking the two-time former champion on five occasions to reach his first ATP Masters 1000 semi-final. Medvedev had lost each of his previous three FedEx ATP Head2Head encounters against Djokovic, but claimed his first victory over a World No. 1 after two hours and 20 minutes to move into the last four.

“It’s definitely the best match of my career. Not in terms of level of tennis, but definitely by the result. [It’s my] first Masters 1000 semi-final, beating No. 1 for the first time in my life,” Medvedev said. “[It’s] just amazing.”

Two days ago, Medvedev owned a 1-11 record against opponents inside the Top 10 of the ATP Rankings. With back-to-back victories over World No. 8 Stefanos Tsitsipas and top-ranked Djokovic, the Sofia Open winner is two wins away from his maiden Masters 1000 crown.

Medvedev is just the second man to defeat Djokovic in nine quarter-finals at the Monte-Carlo Country Club. Belgian David Goffin became the first man to achieve the feat in 2017.

“He’s got a very solid backhand. He doesn’t make many mistakes from the backhand. He hits it very low with depth. A windy day like today, conditions are changing every single game. It’s kind of tough to find the rhythm, and he doesn’t give you much rhythm,” Djokovic said. “He improved his movement a lot since last year. He definitely deserves to be where he is.”

Standing between Medvedev and a place in the final will be another Serbian oppponent; Dusan Lajovic. The World No. 48 backed up his shock win over World No. 5 Dominic Thiem with a 6-4, 7-5 victory against Italian qualifier Lorenzo Sonego.

Alongside his title run in Sofia, Medvedev also advanced to the championship match at the Brisbane International (l. to Nishikori). The four-time ATP Tour titlist owns a tour-leading 21 victories this season (21-6), which is three more than second-placed Roger Federer (18-2) and Stefanos Tsitsipas (18-8). Medvedev was one of just two players (also Shapovalov) to take a set from Djokovic at this year’s Australian Open.

“He played worse than he did the times before and also I’m getting more experienced. I’m starting to make these top guys know that it’s tough to play against me,” Medvedev said. “In Australia he was at his best, but I made him run for the win and I was happy about my game. Here I knew if I kept up the level I had in Australia I would have my chances.”

Under heavy winds on Court Rainier III, Medvedev made the perfect start with a service break in the opening game. The Russian proved impenetrable from the baseline, with Djokovic failing to find the court after pressing with his forehand in extended rallies. Medvedev maintained his level from the back of the court, keeping his error count low to break for a second time and take the opening set. Djokovic committed 21 unforced errors compared to Medvedev’s six in the 39-minute opener.

Read: Why Djokovic’s No. 1 Ranking Is Safe… For Now

But Djokovic found his rhythm, grabbing a 2-1 lead in the second set with impeccable touch. The World No. 1 brought Medvedev into the net behind a well-placed backhand drop shot, before grabbing the break with a backhand lob. Djokovic held his advantage through to 5-4, where he levelled the match with back-to-back aces.

Medvedev was not deterred, though, capitalising on three consecutive unforced errors from Djokovic to take a 3-1 lead in the decider. Two games later, the tenth seed outmanoeuvred Djokovic in net exchanges to grab a second break. Despite failing to serve out the match on his first opportunity, Medvedev broke Djokovic for the fifth time with a backhand winner to claim victory.

Djokovic was bidding to reach his first tour-level semi-final since capturing a record-breaking seventh title at the Australian Open in January (d. Nadal). The World No. 1, who has lifted two titles in Monte-Carlo (2013, ’15), drops to 34-11 at the opening Masters 1000 event of the European clay swing.

Third seeds Jamie Murray and Bruno Soares were clinical on serve Friday to reach the Rolex Monte-Carlo semi-finals for the second time as a team, defeating Argentine-Portuguese duo Diego Schwartzman and Joao Sousa 7-5, 6-2.

Entering this ATP Masters 1000 tournament, Murray and Soares were searching for their best form, having lost four of their previous five tour-level matches together. But after battling through two tight Match Tie-breaks in the first two rounds, the British-Brazilian team defeated Schwartzman and Sousa in 63 minutes.

Murray and Soares made 80 per cent of their first serves, winning 87 per cent of those points to cruise through their service games. The veteran team did not face a break point in the match, breaking Schwartzman and Sousa on all three of their opportunities.

In the semi-finals, Murray and Soares will face Robin Haase and Wesley Koolhof. The Dutchmen ousted Moldovan Radu Albot and Georgian Nikoloz Basilashvili 6-1, 7-5 , also in 63 minutes.

Haase and Koolhof have only competed together once before, losing in the first round at ’s-Hertogenbosch last year. But they have played well, breaking serve four times on Friday. Koolhof reached the Miami final alongside reigning Next Gen ATP Finals champion Stefanos Tsitsipas.

In the only other doubles quarter-final of the day, seventh seeds Nikola Mektic and Franko Skugor upset second seeds Lukasz Kubot and Marcelo Melo 6-3, 7-5 in one hour and 21 minutes. This is the first time Mektic and Skugor are playing together since Basel in 2017.

They will next play Argentines Maximo Gonzalez and Horacio Zeballos, who advanced via walkover.

Less than 24 hours after securing the biggest win of his career against World No. 5 Dominic Thiem, Dusan Lajovic defeated Lorenzo Sonego 6-4, 7-5 to reach his first ATP Masters 1000 semi-final on Friday.

The Serbian was forced to save one set point at 4-5 (30/40) in the second set en route to his 10th tour-level victory of the season after one hour and 47 minutes. Lajovic was competing in his second Masters 1000 quarter-final, following his run to the Mutua Madrid Open quarter-finals last year (l. to Anderson).

Yet to drop a set this week, Lajovic will meet countryman Novak Djokovic or 10th seed Daniil Medvedev for a place in the championship match. Lajovic managed to win one game in his most recent FedEx ATP Head2Head meeting (0-2) against Djokovic in the first round at this event last year. The World No. 48 lost his only previous FedEx ATP Head2Head encounter against Medvedev at the VTB Kremlin Cup last year.

Prior to his arrival at the Grand Prix Hassan II last week, Sonego had reached one tour-level quarter-final. But the Italian qualifier has produced the best tennis of his career to reach back-to-back quarter-finals in Marrakech and Monte-Carlo. Three days ago, Sonego claimed the biggest win of his career against Rolex Paris Masters champion Karen Khachanov.

Did You Know?

If Djokovic defeats Medvedev, Lajovic and the World No. 1 will become the first Serbian pairing to advance to the last four of a Masters 1000 event since the 2012 Rogers Cup. On that occasion, Djokovic defeated countryman Janko Tipsarevic in the semi-finals before cruising past Richard Gasquet to lift the trophy.

Guido Pella is playing the best tennis of his life. The 28-year-old, who became a first-time ATP Tour champion at Sao Paulo in March, is into the quarter-finals of an ATP Masters 1000 tournament for the first time.

But the lefty knows that his next test at the Rolex Monte-Carlo Masters will arguably be one of the toughest he has ever faced, as he gets set to play 11-time champion Rafael Nadal.

“He’s one of the legends of tennis,” Pella told ATP Tennis Radio. “He’s a very special player and to play against him in any tournament is a very special feeling. But I think here in Monte-Carlo, centre court is going to be an amazing atmosphere. Of course the crowd is going to be behind him because he’s the favourite.”

It won’t be the first time Pella has stood across the court from the second seed, having done so at Indian Wells two years ago and Roland Garros last season. In order, Nadal has won their five FedEx ATP Head2Head sets 6-3, 6-2, 6-2, 6-1, 6-1. The Spaniard has won 23 consecutive sets on Court Rainier III in Monaco, without any of those sets getting extended past 6-4.

“I need to do the perfect match to have a chance,” Pella said. “I hope to keep playing like this because I am feeling very good, I am feeling very confident in my game. If I play like this, maybe I will have a chance.”

Listen To ATP Tennis Radio’s Interview With Pella:

Pella suffered what could have been a major mental setback in February. After losing his first three ATP Tour, finals, the Argentine led Juan Ignacio Londero by a set and a break in the Cordoba championship, closing in on a breakthrough.

But Pella could not hold on, finishing runner-up once more. In March, Pella bounced back by triumphing in Sao Paulo.

“It was karma for sure. I lost four finals and in those finals I didn’t play bad, but the fourth final in Cordoba was the worst final for me because I was playing really good. In that match, I couldn’t close it. I was a set up, break up, and well, that’s tennis. These things happen,” Pella said. “In Sao Paulo I did a very good job, a very good tournament overall and I deserved the win. After that I think a new career for me was born. So I’m really enjoying the moment.”

It’s been a magical ride over the past year or so for Pella. Marin Cilic won the first two sets of their match at Wimbledon 6-3, 6-1, before rain suspended play during the third set. The next day, Pella found his best level to oust the Croat, and he hasn’t looked back since. Pella also beat Cilic this week in Monte-Carlo.

“Last year I was playing really good but maybe I didn’t get the results that I wanted. But I think for the past year, year and a half, I’ve been playing really good,” Pella said. “This year is the best with the results, to win a tournament in Sao Paulo, another final in Cordoba, I’m very happy to be here in the quarter-finals in Monte-Carlo. Playing like this, it’s not easy, so I’m very happy.”

Pella is projected to crack the Top 30 of the ATP Rankings for the first time on Monday. But he’s not worrying about that at the moment. He’s fully focused on Nadal.

“I want more. I don’t know where I can go. But I keep playing, I keep winning matches, so let’s see,” Pella said. “For now I’m really happy, I’m really enjoying the Tour right now because I’m winning, so it’s a lot easier that way. But I just want to focus because I have a very tough match and I will try to do the best job that I can.”

Lukasz Kubot and Marcelo Melo were the only seeded team to advance on Thursday at the Rolex Monte-Carlo Masters, as two other veteran pairs fell in straight sets. Melo and Kubot, the second seeds, beat Austrian wild cards Jurgen Melzer and Dominic Thiem 6-3, 6-4 in 66 minutes.

The Polish-Brazilian duo arrived in Monaco having won just one of three previous matches at the ATP Masters 1000 tournament. But Kubot and Melo are through to the quarter-finals without dropping a set.

They have found great rhythm in the past month, making the final of the BNP Paribas Open and the semi-finals of the Miami Open presented by Itau. Kubot and Melo began the week in sixth place in the ATP Doubles Race To London, and they can climb as high as third if they lift the trophy.

Against Melzer and Thiem, Kubot and Melo did well to consistently earn chances in return games, converting on three of 11 break chances in the match. The highest-seeded pair remaining also won an impressive 79 per cent of second-serve points (11/14).

While Kubot and Melo faced little difficulty, fourth seeds Juan Sebastian Cabal/Robert Farah and sixth seeds Henri Kontinen/John Peers were upset.

Brazilian Marcelo Demoliner and Russian Daniil Medvedev (also a singles quarter-finalist) ousted 2018 Nitto ATP Finals qualifiers Cabal and Farah 6-2, 6-4. Entering the tournament, Demoliner had lost four consecutive matches at all levels with three different partners. This is the second time he has partnered Medvedev (2018 Brisbane, l. first round).

Argentine Diego Schwartzman and Portuguese Joao Sousa beat Kontinen and Peers 6-4, 6-3. This is the first time they have competed together. Before this event, the pair combined for a 110-172 tour-level doubles record, with neither player winning a title. Sousa reached the Rome final last year with Pablo Carreno Busta.

In other action, Moldovan Radu Albot and Georgian Nikoloz Basilashvili defeated Hungarian Marton Fucsovics and Argentine Guido Pella 6-1, 6-7(7), 10-6. Albot and Basilashvili won 50 per cent (4/8) of their return points in the Match Tie-break to triumph.

Top seed Novak Djokovic and second seed Rafael Nadal are among the top names in action at the Rolex Monte-Carlo Masters on Friday, when all singles and doubles quarter-finals will be played.

Djokovic continues his quest for a third Monte-Carlo title against tenth seed Daniil Medvedev of Russia. The Serbian leads their FedEx ATP Head2Head rivalry 3-0, but this will be their first match on clay. Djokovic shook off the clay rust in his opening-round clash with Philipp Kohlschreiber and rounded into form with a dominant victory over American Taylor Fritz on Thursday.

Who will win the fourth @FedEx ATP Head2Head battle between these players?#RolexMCMasters

— ATP Tour (@ATP_Tour) April 18, 2019

Medvedev has also been highly impressive. The World No. 14 dropped five games in his first two rounds and then took out sixth seed Stefanos Tsitsipas of Greece for his berth in the last eight. The Russian is the first player this season to pick up 20 match wins, but is looking for his first Top 5 win in two years.

Nadal seeks to move closer to a 12th title at this event when he faces Guido Pella. The Spaniard leads their FedEx ATP Head2Head series 2-0. Pella has been a force on clay this season, winning his first ATP Tour title at the Brasil Open (d. Jarry) and scoring a Top 15 victory this week over Marin Cilic en route to the quarter-finals. Nadal, as usual, has been dominant from the first ball in Monte-Carlo. He’s dropped seven games in his first two matches and is on a 17-match winning streak on Court Rainier III.

Dusan Lajovic of Serbia and Italian qualifier Lorenzo Sonego open up play on Friday. Lajovic scored his first Top 5 win against Dominic Thiem to move into the last eight, while World No. 96 Sonego has won all of his main draw matches without dropping a set. The Serbian seeks his first Masters 1000 semi-final, while Sonego aims for his first ATP Tour semi-final.

The final match of the day will see ninth seed Borna Coric of Croatia take on 13th seed Fabio Fognini of Italy. Fognini won their lone FedEx ATP Head2Head meeting five years ago on the red clay of Umag. The Italian has turned his season around after arriving in Monte-Carlo having lost seven of his past eight matches, upsetting third seed Alexander Zverev to reach his fifth ATP Masters 1000 quarter-final. Coric has spent more than eight hours on court to move into his first Monte-Carlo quarter-final and continues to increase his level with each match.

Second seeds Lukasz Kubot / Marcelo Melo and third seeds Jamie Murray / Bruno Soares are among the top doubles teams who will take to Court des Princes. 

ORDER OF PLAY – FRIDAY, APRIL 19, 2019

COURT RAINIER III start 11:00 am
Dusan Lajovic (SRB) vs [Q] Lorenzo Sonego (ITA) 
[1] Novak Djokovic (SRB) vs [10] Daniil Medvedev (RUS) 
Guido Pella (ARG) vs [2] Rafael Nadal (ESP) 
[9] Borna Coric (CRO) vs [13] Fabio Fognini (ITA)

COURT DES PRINCES start 11:00 am
[3] Jamie Murray (GBR) / Bruno Soares (BRA) vs Diego Schwartzman (ARG) / Joao Sousa (POR) 
Robin Haase (NED) / Wesley Koolhof (NED) vs Radu Albot (MDA) / Nikoloz Basilashvili (GEO) 
[7] Nikola Mektic (CRO) / Franko Skugor (CRO) vs [2] Lukasz Kubot (POL) / Marcelo Melo (BRA) 
After Suitable Rest – Maximo Gonzalez (ARG) / Horacio Zeballos (ARG) vs Marcelo Demoliner (BRA) / Daniil Medvedev (RUS) 

Fabio Fognini failed to take a set off Alexander Zverev in their first two FedEx ATP Head2Head meetings. But the Italian broke through in style against the 21-year-old on Thursday at the Rolex Monte-Carlo Masters.

In front of an energised crowd on Court Rainier III, Fognini secured 75 per cent of first-serve points (30/40) to defeat Zverev 7-6(6), 6-1 in 90 minutes. Fognini has now reached five ATP Masters 1000 quarter-finals, which include his run to the semi-finals at the Monte-Carlo Country Club in 2013 (l. to Djokovic).

Fognini entered the tournament with seven losses in his past eight tour-level matches and trailed Andrey Rublev 4-6, 1-4 in his first-round match. But after his first win over a Top 3 opponent since his victory over then-World No. 1 Andy Murray at the 2017 Internazionali BNL d’Italia, Fognini is one win away from a return to the last four in the Principality.

The World No. 18 will meet ninth seed Borna Coric in the quarter-finals. Fognini defeated Coric in their only previous FedEx ATP Head2Head clash at the 2014 Plava Laguna Croatia Open Umag.

The Croatian advanced to his second straight Masters 1000 quarter-final after one hour and 41 minutes, saving all three break points he faced to beat Pierre-Hugues Herbert of France 6-4, 6-2. Coric also reached the last eight at the Miami Open presented by Itau last month, beating Nick Kyrgios in three sets before a straight-sets loss to #NextGenATP Canadian Felix Auger-Aliassime.

Did You Know?
With qualifier Lorenzo Sonego also advancing to the last eight, two Italians are into the Monte-Carlo quarter-finals for the first time since 1978, when Corrado Barazzutti and Adriano Panatta accomplished the feat.

Dusan Lajovic reached his second ATP Masters 1000 quarter-final on Thursday, upsetting fourth seed Dominic Thiem 6-3, 6-3 at the Rolex Monte-Carlo Masters.

The 28-year-old saved seven of nine break points and broke last year’s Roland Garros runner-up on five occasions to advance after one hour and 32 minutes. Lajovic entered the match winless in five FedEx ATP Head2Head record against Thiem, but reached his second quarter-final in the past three Masters 1000 events on clay.

“I’m very happy today. I didn’t expect this, especially not in two sets against a player like Dominic,” Lajovic said. “This was for sure my best match in my life, I think. I produced some great tennis from the beginning until the end of the match and I’m very happy to be in the quarter-finals in Monaco.”

Thiem, the recent BNP Paribas Open champion, figured to be a strong threat in the Principality. But Lajovic took full advantage of Thiem’s deep court-positioning, playing aggressive tennis and winning some of the best rallies of the tournament thus far. Lajovic did well to consistently battle into the Austrian’s service games, winning 53 per cent of his return points in the two-setter. The Serbian was also impressive in his second-round victory against 16th seed David Goffin.

“It was very windy today and it was not easy to hit the ball cleanly. I had more success there and I was moving the ball through the court very well,” Lajovic said. “I was able to dominate with my forehand today and this was the key in the match.”

At last year’s Mutua Madrid Open, Lajovic notched five victories from qualifying to reach the last eight. Lajovic edged Juan Martin del Potro in Madrid en route to the quarter-finals before suffering a three-set loss to Kevin Anderson.

Thiem was bidding to post his 10th tour-level win of the season (9-6) and reach his second straight quarter-final at the Monte-Carlo Country Club. Thiem had reached the quarter-finals or better at five of the past seven Masters 1000 events on clay, dating back to his appearance in the last eight at the 2016 Internazionali BNL d’Italia (l. to Nishikori).

Lajovic will meet Lorenzo Sonego of Italy for a place in the semi-finals. The 23-year-old qualifier advanced to his maiden Masters 1000 quarter-final after 84 minutes, dropping only four points behind his first serve (28/32) to overcome Cameron Norrie 6-2, 7-5. Sonego is yet to drop a set in the main draw, defeating Cameron Norrie in the third round for his best result at a Masters 1000 tournament.

“I know that [from what] I’ve seen, it’s very good and he’s going to be a very good player. He’s already a very good player,” Lajovic said. “He’s young, he’s playing one of the best tournaments of his career so it’s not going to be easy. I’ll need to keep my focus, to go on the court and hopefully play like today.”