Andy Murray and Novak Djokovic dropped outside the ATP top 10 for the first time in years in the latest rankings released on Monday.
Thirty-year-old Murray plummeted from third to 16th after not playing since July with a hip injury.
The Scot’s last appearance outside the top 10 was in October 2014.
The three-time Grand Slam winner last appeared on court at Wimbledon, losing in the quarter-finals to American Sam Querrey.
Shortly after that, he was nudged off the top of the world rankings by Rafael Nadal who sealed the end-of-year top spot at the Paris Masters last week.
Murray is due to face world No. 2 Roger Federer in a charity exhibition match in Glasgow on Tuesday before he starts his preparations for the Australian Open by playing in Brisbane.
Djokovic, struggling with an elbow injury, was also last seen in action at Wimbledon when he retired against Tomas Berdych the in quarter-finals.
The 12-time Grand Slam winner ends the year in 12th, down five places, for his lowest ranking since March 2007.
Djokovic is hoping to make a comeback at the exhibition World Tennis Championship in Abu Dhabi next month.
Here are the rankings as on November 6:
1. Rafael Nadal (ESP) 10645 pts
2. Roger Federer (SUI) 9005
3. Alexander Zverev (GER) 4410 (+1)
4. Dominic Thiem (AUT) 3815 (+2)
5. Marin Cilic (CRO) 3805
6. Grigor Dimitrov (BUL) 3650 (+2)
7. Stan Wawrinka (SUI) 3150 (+2)
8. David Goffin (BEL) 2975 (+2)
9. Jack Sock (USA) 2765 (+13)
10. Pablo Carreno (ESP) 2615 (+1)
11. Juan Martţn Del Potro (ARG) 2595 (+6)
12. Novak Djokovic (SRB) 2585 (-5)
13. Sam Querrey (USA) 2535
14. Kevin Anderson (RSA) 2480 (+2)
15. Jo-Wilfried Tsonga (FRA) 2320
16. Andy Murray (GBR) 2290 (-13)
17. John Isner (USA) 2265 (-3)
18. Lucas Pouille (FRA) 2235
19. Tomas Berdych (CZE) 2095
20. Roberto Bautista (ESP) 2015 (+3)
