Schedule of play:
Serena Williams vs. Samantha Stosur
A rematch of the 2011 US Open final, Serena Williams will be making her appearance since her debut in 2000. Serena and Montreal seemed to have differing paths as the American is either injured, or chose to skip the event when it is held there. Stosur will provide a stern test for Serena, who is not in peak form yet. Nevertheless, Stosur's form is even worse, losing to unheralded Osaka last week, so I think Serena will be fine. She might struggle at first, but should be able to win this.
Pick: Williams in 3 sets
Jelena Jankovic vs. Sloane Stephens
Jelena Jankovic will be eager to put away her atrocious grass season and start anew on her favourite hard courts. Immediately, she will face a tough opponent in Sloane Stephens, who annihilated Aleksandra Wozniak. Jelena's confidence must be a bit fragile given her winless grass season, but hard courts is where she excels. Sloane will push her, but Jelena thrives on pace, and will grind Sloane to make errors. If she's motivated enough, Jelena should be able to take this.
Pick: Jankovic in 3 sets
Sabine Lisicki vs. Madison Keys
Battle of the big servers here. Sabine Lisicki proved everyone wrong by demolishing Errani, and looks to be in good form on hard courts. Madison Keys got lucky that Kuznetsova got injured, gifting her a second round place. On current form, I believe Lisicki is playing better. Keys is still under an injury cloud that forced her out of Wimbledon. It might flare up any moment. Sabine, on the other hand, is taking baby steps in winning matches she's supposed to win, and also causing an upset over Errani. When the German is confident, she will be lethal.
Pick: Lisicki in 3 sets
Sure win bets: Venus Williams, Petra Kvitova, Caroline Wozniacki
Upset alert: Madison Keys, Dominika Cibulkova, Carla Suarez Navarro