Milos Raonic is on the verge of history.  With a win on Friday at Wimbledon, he would become the first player representing Canada to reach the final of a men's tennis Grand Slam.  Canadian-born Greg Rusedski made the 1997 U.S. Open final, but by that time he was competing under the British flag. Canada's Eugenie Bouchard reached the Wimbledon women's final in 2014.  It won't be easy for Raonic.  His opponent, Roger Federer, has dominated Raonic in his career, winning nine of 11 matches.  The Swiss star is also playing for history. With two more wins, he can break the all-time record for Wimbledon men's titles, which he currently shares with Pete Sampras and 1880s player William Renshaw at seven apiece.  If he beats Raonic, Federer will break Jimmy Connors's all-time Wimbledon match wins record of 84.  Federer has already won a record 17 Grand Slam men's titles, and his career record in majors is 307-50.  Although Raonic doesn't have much to brag about in his career against Federer, the 25-year-old did come away with a victory in the final of the Brisbane International in January — the last time the two met.  Raonic's only other victory against Federer came in the quarter-finals at the Paris Masters in 2014.  The No. 6-seeded Raonic is making his second appearance in the Wimbledon semifinal. In 2014 he lost in straight sets to Federer.  Raonic, who was born in Montenegro and now calls Thornhill Ont., his hometown, is having a strong year. He's 31-8 overall in 2016, including 8-2 in Grand Slam matches, and made a semifinal appearance at the Australian Open. Raonic has also come up clutch in close contests, winning a deciding third or fifth set eight of 10 times this season.  Raonic's impressive run this year at Wimbledon includes a memorable boomerang shot in the quarter-finals against Sam Querrey.  You know you've hit a good drop volley when it lands back on your side of the net...Take a bow @milosraonic https://t.co/CYwFYA09Ku  The No. 3-seeded Federer is 16-6 this season, including 5-1 in Grand Slam action.  The Raonic-Federer match begins at 8 a.m. ET on Friday, followed by the other semifinal between No. 2 seed Andy Murray and No. 10 Tomas Berdych.  The winners will meet in Sunday's final.
Milos Raonic can make Canadian tennis history with a win over Roger Federer in the semifinals at Wimbledon on Friday. However, Raonic has only won two of 11 career matches against the Swiss star.