The rapid success has surprised Davis Cup captain Martin Laurendeau, who achieved a career high of No. 90 in 1988.
With Laurendeau at the helm, Canada surfaced in a maiden Davis Cup semifinal in 2013.
"We had a few athletes spread out during the generations doing a few good things here and there, but never really was there a club like this where they broke through on the international stage at the same time," Laurendeau told CNN.
The inevitable question is, why now?
"Tennis Canada's development programs, especially in Montreal, have been excellent, but in many ways the best players -- Raonic in Toronto, Bouchard in Montreal and Pospisil in Vancouver -- owe the most to their families and individual coaches," Canada's longest serving tennis writer, Tom Tebbutt, told CNN.
Touching more on Tennis Canada's contribution, Laurendeau brought up several factors.
The focus, he said, has shifted to high performance and development.
More resources, he added, have allowed the governing body to hire experienced coaches from other countries -- Laurendeau cited Louis Borfiga, who worked extensively in France -- and junior players can attend the tournaments they want rather simply choose the cheapest option.
"Louis came in and helped to change the mentality of the Canadian tennis players," said Laurendeau. "I do believe we believe more in our capabilities to break through.
"The mentality is a big part of it, definitely."
To that end, Bouchard wasn't just happy to reach the Wimbledon final, and Raonic said Wimbledon was bittersweet.
He took pride in getting to the last four but was "upset" with his straight-set loss to Federer.
Thus instead of doing media rounds when he got back home, Raonic almost immediately went straight back to training.
"As soon as I got my time off, I actually left Canada," said Raonic. "I wanted to be away from the things that might follow after tennis.
"When I came back and started training, I trained away from the tennis facility and actually (trained) where Toronto's (MLS) team trains.
"I think it was a great result in general at Wimbledon, but I was upset with the way it finished so I wanted to put that behind me and get my nose back into the work."
Now, according to Laurendeau, the key is to maintain the momentum.
Having a major star or handful of pros thriving is no guarantee of sustained success.
Take Sweden or Brazil.
Sweden, the home of Bjorn Borg and Stefan Edberg, doesn't have a men's player in the top 200. Brazil, meanwhile, couldn't capitalize on Gustavo "Guga" Kuerten's enormous popularity.
Helping Canada is its tennis infrastructure -- a major training hub lies in Montreal -- and more people in the country, according to information provided by Tennis Canada, are playing the sport.
The performances of Raonic, Bouchard and Pospisil should maintain the trend for the foreseeable future.
"When things get hot but there's no structure behind it, well, there are so many options for kids to go into that are exciting," said Laurendeau. "You want to pick up the game, you go here. How old are you? You can go here. Where do you live? You can go here.
"That's very important. When I look back at the Guga era, he was probably one of the greatest known sports figures in the world at one time.
"Especially in Brazil, tennis was very popular. Why didn't they see a boom behind Guga? It was because that was lacking. It's important for us to have a structure in place -- and we do have it in place."