At the start of the 2013 season, Federer had won 76 titles and more than $76 million in prize money. Raonic, three titles and just under $2 million.
Federer has won all three of their previous clashes, all in 2012.
But the Swiss world number two and the giant Canadian are only too aware that sometimes pure statistics do not reflect the true nature of tennis.
In all three of their matches at Halle, Madrid and Indian Wells, the world number 15 had Federer on the ropes. So much so, Federer acknowledged that he won games he should have lost.
"I've had some tough matches with him in the past," Federer said of his expectations facing the 1.96-metres (6-foot-5) tall 22-year-old. "All of them went the distance. Some of them I should have lost, maybe one or two.
"Indian Wells, I felt like I was more in control than the other two. In Madrid I was in a lot of trouble. Halle was extremely close."
Raonic, who told Reuters earlier in the tournament that Monday's clash was the sort of match he needed to win to "kick down the door" to reach the top 10, added the experience of playing so well against Federer last year would be beneficial.
"I think I played well in the other ones," Raonic said.
"I think I got pretty damn close the one time in Madrid. I got pretty close in Halle.
"I just know how to deal with it. I think I have a higher tolerance within myself and a higher belief within myself stepping up against Roger."
The winner of the clash will face a Frenchman in the quarter-finals, either seventh-seed Jo-Wilfried Tsonga or ninth-seeded compatriot Richard Gasquet.
US Open champion Andy Murray will face an exhausted Gilles Simon in the final match on Hisense Arena.
The 14th-seeded Frenchman, who beat compatriot Gael Monfils in a marathon five-set clash on Saturday, said he was in pain everywhere from cramping and pointing to his arms, legs and shoulder.
"Cramp here, I don't even know it is possible to cramp here," he said to laughter after he pointed to his jaw.
"I don't have a lot of chance to win this one, but this is my job to go on the court and to do the maximum to bother him and to give him a hard time."
Women's champion Victoria Azarenka, who struggled against American Jamie Hampton in the third round, is also in fourth round action on Monday and will play a confident Elena Vesnina, who won her first WTA title in Hobart before the grand slam began.
"Elena is playing one of her best tennis in her life, and is especially very confident after winning title," Azarenka said.
"Fourth round of the grand slam, second week, everybody wants to win and everybody is playing good.
"I'm looking forward to it."
Azarenka's potential semi-final opponent Serena Williams is also back on court facing an in-form Maria Kirilenko.
"Maria is playing consistent tennis, especially the past 16 to 18 months, she's been so consistent," Williams said.
"So my goal is just to be really focused against such a player that's doing so well." (Editing by Patrick Johnston)