Rogers Cup finalist from ten years ago, Maria Sharapova couldn't use a wild card as she would have wanted, losing in the opening round to the 16th seed Anett Kontaveit 4-6, 6-3, 6-4 after grueling two hours and 41 minutes.
Facing each other for the first time since Stuttgart 2017 when Sharapova made her comeback, the Estonian overcame a slow start to emerge as the winner, saving five out of eight break points and stealing Sharapova's serve four times from 12 opportunities to earn the spot in the second round.
Toronto was the sixth tournament for the Russian in 2019 and she is yet to find the desired rhythm after injuries, wasting some seven game points at 4-4 in the decider to lose serve and allow Kontaveit to forge the crucial advantage that carried her home in a high-quality and tight encounter.
Maria broke at 15 in the first game of the match with a stellar return winner, losing the advantage in the very next game after a double fault that brought Kontaveit back on the positive side of the scoreboard. Four good service games later, Sharapova broke again with a forehand crosscourt winner that sent her 4-3 up, saving a break point in game ten with a service winner and landing another booming forehand for a 6-4.
Sharapova saved three break chances in the second game of the second set, securing a break in the next game after a forehand error from Anett and moving closer and closer to the finish line. The Estonian was ready to fight, though, pulling the break back following a forehand error from Maria in the next game to level the score at 2-2.
The 16th seed repelled five break points in the fifth game and grabbed a break at 4-3 when Sharapova sent a backhand wide, closing the set with a hold at love to take it 6-3 and send the clash into a decider. There, both players served well in the first eight games and the winner was decided in that epic game at 4-4 when Sharapova squandered those game chances that could have sent the pressure to the other side of the net.
Kontaveit survived that all and earned a break after forcing an error from Maria, moving 5-4 up and sealing the deal with two winners at 30-30 in the next game to start a massive celebration.