Djokovic breaks Nadal record with 'ugly' De Minaur win, Ruud ready for 'David v Goliath' clash

Novak Djokovic progressed to his 77th ATP Masters 1000 semi-final – breaking Rafael Nadal’s record – following a hard-fought 7-5 6-4 win over Alex de Minaur in Monte Carlo.

The world No. 1 advances to his first semi-final in the principality since 2015, and will meet either Casper Ruud or Ugo Humbert in the last four.

Speaking after the match, Djokovic said: “It was tough for both of us; he’s one of the quickest players on tour. He gets a lot of the balls back which 99% of the other players don’t.

“He surprised me with several passing shots, particularly in the second set when I was up a break.

“He said at the net that it was ugly, and in the second set I think it was because we didn’t play at high level. We made a lot of unforced errors, with some consecutive breaks of serve.

“You kind of expect that for clay, but maybe not this many. Again, a win is a win and I’m glad to go through.

“I love this tournament; I know this club very well and I’ve trained for many years here. The last seven or eight years have been tough for me to win two or three matches consecutively, but I’m in another semi and I look forward to it.”

The first set went with serve for the first 11 games, with neither player giving much away in the opening exchanges.

De Minaur was acquitting himself well against the world No. 1 and swatted away a set point in the 10th game, in what was proving to be a bruising first set that had lasted one hour, with the Serbian leading 6-5.

The Australian was showing impressive resolve not to buckle under Djokovic’s pressure, before eventually succumbing after a fourth set point.

De Minaur was starting to lose his range and somehow missed a wide-open court with a routine forehand return, leaving the world No. 11 a set and break down.

However, it was Djokovic’s turn to miss a routine overhead shot, leaving the Australian with two break points.

He prevailed on the first with the Serbian sending a backhand astray, and this set also threatened to go the distance.

A fourth break in five games came and went as Djokovic sent a return long, as De Minaur stayed within range at 3-2.

Djokovic was clearly feeling the strain of this vigorous contest, and despite looking like he may have been pulling away at 4-2, De Minaur responded with an immediate break back at 4-3.

The Serbian was looking more like himself when he claimed an emphatic hold to love, moving one game away from victory at 5-4.

And Djokovic prevailed on the first of two match points to seal a last-four berth as De Minaur netted a return.

Casper Ruud booked his place in the semi-finals and a meeting with Djokovic after beating Ugo Humbert 6-3 4-6 6-1 in a keenly-contested quarter-final.

After a superb 6-4, 6-2 victory over Hubert Hurkacz, the Norwegian made to sweat at times in this victory over the Frenchman.

It was looking very straightforward when Ruud wrapped up the first set in 35 minutes and looked imperious on his serve, breaking Humbert twice to draw first blood.

The world No.10 moved 1-0 in front after prevailing on the first of his two set points, as Humbert netted a return.

Ruud moved a set and a break up after Humbert failed to find the range with his returns against the Norwegian’s aggressive approach.

However, a few unforced errors were starting to creep into the Norwegian’s game and allowed Humbert to take his first break of the match at 2-1 down.

Humbert followed that up with an emphatic hold to 40 and sensationally managed to break Ruud again to flip the second set in his favour at 3-2.

Momentum was firmly with Humbert at that point, as he staved off three break points to take a hold at 4-3 and had three set points in the bank after scoring with his first ace of the match.

He restored parity on the second of those and left Ruud rattled heading into the deciding third set.

After holding his own at the start of the decider, Ruud claimed a crucial break in the fourth game and followed that up with a hard-fought hold at 4-1 to move two games away from victory.

Ruud eventually got the job done on his second match point to tee up a tantalising last-four clash with the world No.1.