He worked for Rogers Sportsnet as an analyst while recovering from injury for their broadcast of the 2011 Canadian Open. In November 2011, Raonic won an exhibition match against his childhood idol, Pete Sampras, which was dubbed "The Face Off." In 2012, he took up residence in Monte Carlo, Monaco in a 50 metre (538 sq ft) apartment, located minutes away from the Monte Carlo Country Club—his "home" tennis club and the site of the Monte-Carlo Masters tournament—and Stade Louis II, which he uses for off-court training. Raonic was in a relationship with Canadian model Danielle Knudson.
By the summer of 2008, Raonic had received scholarship offers from several colleges, including the University of Michigan, Princeton, and Northwestern University, and committed to play for the University of Virginia that fall while studying finance. Just two weeks before school started, he consulted his parents about his plan to turn professional instead. Raonic and his parents agreed that he would take correspondence courses in finance from Athabasca University while starting a professional tennis career, setting a deadline of two years for reaching the top 100. During that summer, his world ranking ranged between No. 915 and No. 937. Raonic reached the top 100 in January 2011, around five months later than the target deadline. He thus turned down the scholarships and turned professional, agreeing to be represented by the sports agency SFX. University of Virginia men's tennis coach Brian Boland later commented that "I have only seen two guys turn down scholarships and then succeed quickly on the Tour: Sam Querrey and Milos Raonic."
Three years prior, in 2011, Raonic had set a personal goal of reaching the year-end ATP Finals, where only the top eight players earned a spot. Heading into the last ATP 1000 event of 2014, the Paris Masters, Raonic trailed Ferrer for the eighth spot, and needed a deep run to surpass him. He beat Sock and Roberto Bautista Agut to set up a quarterfinals match against No. 2 Federer, who had beaten him in all six previous meetings. Needing a win to avoid being eliminated from contention for the ATP Finals, Raonic won in straight sets. His victory was hailed as "a career-defining win." In the post-match interview, Raonic was asked to rank this victory in his career. He replied: "Considering all the circumstances around it, I think this was the biggest win for me." He went on to beat No. 5 Berdych in the semifinals to earn a spot in the second ATP 1000 final of his career. He lost to Djokovic in the final, but secured his place in the 2014 ATP Finals. He is the first Canadian to reach the ATP Finals, and the first player born in the 1990s to do so. Anticlimactically, Raonic withdrew from the tournament due to a leg-muscle tear prior to his match against Nishikori, after losses to Federer and Murray.
In 2011, while recovering from a hip injury sustained at Wimbledon, Raonic decided to become involved with philanthropic work, focusing on helping disadvantaged children. The following year, in 2012, he launched the Milos Raonic Foundation, which aims to "support children from disadvantaged backgrounds in order to remove economic, physical and other barriers that might prevent them from becoming healthy, productive members of society. ... In the initial stages of its work, the foundation will focus, in particular, on children with physical disabilities." As of 2016, the foundation had awarded $120,000 in grants to the Holland Bloorview Kids Rehabilitation Hospital, and $30,000 to the Canadian Paralympic Committee. Raonic and his parents are the three directors of the foundation, which has partnered with ATP Aces for Charity.