Novak rallied from a set and a break down and saved two match points before going on to beat Ernests Gulbis 5-7, 7-6 (7), 6-1 in the Rogers Cup QF.
Novak beat world no.35 Jack Sock 6-2, 6-1 in just 54 minutes to move into the Rogers Cup quarter-finals.
Nole and Janko upset no.4 seeds Rohan Bopanna (IND) and Florin Mergea (ROM) 6-3, 5-7, 10-3 to reach quarter-finals in Montreal.
Nole advanced into the Canada Masters last 16 with a 6-3, 7-6 (4) victory over Thomaz Bellucci (BRA) on Tuesday night.
Serbian duo of world no.1 Novak Djokovic and former world no.8 Janko Tipsarevic beat Viktor Troicki and Andreas Seppi 6-4, 6-3.
Novak is a top seed and has a first round BYE. He will open campaign against Thomaz Bellucci (BRA) on Tuesday.
Novak will be leading the Singapore Slammers in the second season of the 2015 Coca-Cola International Premier Tennis League (IPTL).
Novak starts his US Open Series campaign at the Rogers Cup, taking place in Montreal, Canada, from August 10-16.
Nole won the Best Male Tennis Player award at the 23rd annual awards show at the Microsoft Theater.
In the latest ATP Ranking list, Djokovic has 13,845 points. He is followed by Roger Federer (9,665) and Andy Murray (7,810).