Novak Djokovic is targeting a 100th ATP title this weekend but says the imminent prospect of being the final active player from the ‘Big Four’ of men’s tennis feels “overwhelming”.

For many years, Djokovic had intense and rewarding rivalries with Roger Federer, Andy Murray and Rafael Nadal, who joined him in the famed quartet.

Djokovic beat Czech teenager Jakub Mensik 6-7 (4-7) 6-1 6-4 on Friday to reach the Shanghai Masters semi-finals and is still chasing tour success.

The win came a day after Nadal announced he will retire in November.

Federer retired in 2022, while Murray ended his own career in August.

“[Nadal] has been my greatest rival. The rivalry I had with him has impacted me the most in my career by far,” Djokovic said after his win against Mensik.

“We knew that that moment is coming sooner than later, but it’s still a shock, you know.

“Roger a few years ago, when he announced retirement, and Andy as well this year. I mean, it’s a bit overwhelming for me to be honest.

“I don’t know what to make out of it. I still enjoy competing. But part of me left with them, a big part of me.”

Serbia’s Djokovic has won 24 Grand Slam titles – a men’s record – and claimed a long-awaited Olympic gold earlier this year.

The 37-year-old will face American world number seven Taylor Fritz in Saturday’s semi-final as he bids for a landmark 100th title.

Fritz, 26, comfortably beat Belgium’s David Goffin 6-3 6-4 on Friday to book his place in the last four. It extended a run that has seen Fritz progress past the third round for the first time in Shanghai.

Djokovic, who will now compete in a 78th Masters 1,000 semi-final, said he was motivated by matches against the upcoming generation.

“It keeps me going, and pushes me to really dig deep, and to show to the world that I’ve still got it in my legs, that I can still go the distance with the young guys,” he said.

“I’m super glad that I managed to win this very challenging match.”

Mensik, 19, held his nerve in the opening set against Djokovic.

Yet Djokovic, a record four-time winner of the tournament, was able to regroup after a scrappy performance in the tie-break and breezed through the second set, before putting the match to bed after two hours and 21 minutes.

Although US Open runner-up Fritz might provide a tough test for Djokovic, the decorated veteran holds a 9-0 career record from their past meetings.

Fritz broke in the second and sixth games to take the opening set against 66th-ranked Goffin.

Goffin looked stronger as the match continued, but he could not quite find the same form that brought him victory against second seed Alexander Zverev in the previous round.

“I’m really happy with how I played,” said Fritz.

“[Goffin’s] such an incredible returner, I had to stay extremely focused, even more focused than normal on my service games.”

Saturday’s first singles semi-final features Italy’s world number one Jannik Sinner and Czech player Tomas Machac, who beat Carlos Alcaraz on Thursday.