Reigning US Open champion Emma Raducanu fails to reach the quarter-finals of the Madrid Open

Emma Raducanu and Jack Draper provided signposts towards the future, but last night at the Madrid Open old man Andy Murray was showing that he still has it.

Having made a late decision to resume playing on clay, Murray set up a reunion with Novak Djokovic by beating world number 16 Denis Shapovalov to reach the men’s third round.

Murray will face Djokovic for the first time since early 2017 after thrilling the crowd with a 6-1 3-6 6-2 victory over the talented Canadian that finished at 12.34am.

The 34 year-old Scot, who does not even plan to play at Roland Garros this year in order to concentrate on the grass, already looks revitalised by his time with Ivan Lendl. His movement on the brown dirt continues to be a revelation after years of hip problems.

The search for a deep run at a tournament outside a Grand Slam goes on for Raducanu, who agonisingly missed out on the women’s quarter finals.

A third straight win at an event beckoned for the first time since New York, only for her to be edged by Anhelina Kalinina, one of the Ukrainians currently competing on the tour with a fire inside.

Raducanu cited more physical issues as she narrowly went down 6-2 2-6 6-4 after two hours and eighteen minutes, during which there was precious little to separate the two players.

Having felt pain in her lower back earlier this week, the US Open champion left the court for treatment after the first set, and was much improved thereafter.

‘Throughout the week I have been carrying some niggles,’ said Raducanu, ‘It’s kind of taking its toll, all of the matches at this kind of level. I think that’s a good thing, I feel like I’m going through this and my body is building with each match I play.

The 34-year-old set up a first clash with Novak Djokovic in more than five years 

‘A lot of the time with me it’s just overload. I was really struggling to move out wide, but credit to her, she gave me nothing.’

Kalinina is not one of the better-known Ukrainian women but showed why she has been good enough to beat three Grand Slam champions in a row.

She struck the ball superbly in the opening set and Raducanu, who had been holding her lower back early on, had little response.

After the hiatus caused by her treatment the Kent teenager closed off her opponent’s highly effective cross court backhand and served more consistently, extracting far more errors from the other end.

Louis Cayer, the veteran LTA coach being used as a part-time technical consultant, was watching courtside and would have been pleased.

Kalinina left the court after the second set and she rediscovered her range to go 3-1 up. The pendulum swung both ways thereafter in the kind of match which showed why women’s tennis has so few players able to establish any kind of superiority right now.

Emma Raducanu (above) failed to progress through to the quarter-finals on the Madrid Open 

Earlier Draper showed that he will already be a threat at Wimbledon this summer, for which he looks set to be automatically qualified.

The 20 year-old’s rapid improvement was further emphasised when he came close to defeating world number eight Andrey Rublev before being pipped 2-6 6-4 7-5 in the second round.

Having started the season at 265 he is now on the cusp of the top 100, which ought to see him straight into The Championships without the need of a wildcard.

The power of his southpaw serve and forehand had the Russian – whose own groundstrokes are huge – rocked back on his heels for a lot of the match.

‘I’m gutted that I couldn’t sustain my level and come through the match, but at the same time, this week’s a new experience for me, being on the clay in a top event like this and playing a top-10 player,’ he said.

Raducanu (R) lost 6-2 2-6 6-4 to Anhelina Kalinina (L) after two hours and eighteen minutes