First set :
Shapovalov came out the faster of the two playing his aggressive style of tennis and managed to get breakpoints right away on Simon's first service game. He would end up breaking the Frenchman's serve with a superb winner.
The Nice, France native finally managed to get on the scoreboard and then went looking for the break to get back in the set. He managed to do just that breaking the Tel Aviv native to love to even the setback at 2-2.
Both players would go on to trade breaks but the Nassau, Bahamas resident would get the double break when the Monte Carlo resident hit a ball that went out.
The Canadian would serve for the set at 5-2 and would take it finishing the game with a volley winner at the net to win it 6-2.
Second set :
The second set was quite the opposite of the first set as Simon would turn the tables on Shapovalov winning his first service game and managing to get the early break to lead 2-0 when the Canadian would over hit a backhand that went long.
The 35-year-old would manage to hold serve and save several breakpoints from the 21-year-old forcing his opponent to hit unforced errors. The 11th ranked player in the world finally got on the scoreboard and managed to get three breakpoints on the 54th ranked player service game.
Simon would save all three break points playing some great tennis and forcing the Canadian to make mistake with his groundstrokes. Shapovalov would get a second chance at a breakpoint to go back on serve and luckily he would catch a break as one of the Frenchman shots would hit the net and the set was back on serve at 3-2.
The Boulogne Billancourt resident would respond once again but getting breakpoints in the next game after the Canadian would double fault. He would end up breaking to take a 4-2 lead after playing a great rally and finishing the point with a passing shot for a winner with Shapovalov at the net.
The next game once again it was the Canadian motivated to stay in the set and was working to get the break back. Simon was missing a lot of shots and giving chances to Shapovalov to stay in the set. The Frenchman would save both with two huge serves that were unreturnable.
He would end up holding his serve winning game point with a forehand down the line to take a 5-2 lead. The 9th seed would hold his next service game and force the Frenchman to serve it out.
Simon would have three set points in the next game at 5-3 but Shapovalov would save all three playing some great tennis and hitting some amazing winners.
He would save five breakpoints and end up breaking the Frenchman serve. He would finish a run of five straight games breaking Simon at 5-5 to lead 6-5 and serve it out to take it 7-5.
Third set :
The Canadian took the momentum into the third set getting break chances in the first game once again but the Frenchman was up to the task of saving them. Both players would hold their opening service games and Shapovalov would get the first break of the set when he would hit a return winner to set up breakpoint and Simon would hit a forehand long to make it 2-1 for the Canadian.
It would stay on serve until 3-2 when the Nassau, Bahamas resident would give the Frenchman a chance to get back into the set and would break to even the set at 3 when the Canadian would hit another unforced error.
At 5-6 Shapovalov would serve to force a tiebreak but Simon had other plans and would push for the break to take the third set. The Frenchman would have two set points when the Canadian would hit a volley into the net.
The Frenchman would win the third set when the 9th seed would send a forehand long to take it 7-5.
Fourth set :
We would enter the fourth set with Shapovalov hungry to end it while Simon was looking to pushing the match to a deciding 5th set. The Frenchman got early breakpoints once again but the Canadian did a good job forcing Simon to hit a return long.
The next game the Canadian had break chances of his own and would make good on it when the Frenchman would hit a ball into the net to take an early 2-1 lead.
Simon would respond in the next game getting a breakpoint when he was able to lob a ball over Shapovalov head and would level the set when the Canadian would miss a forehand. The 11th ranked player would respond immediately breaking back in the next game when the Frenchman would send a shot wide on a breakpoint.
Shapovalov would hold to make it 4-2 and then increase his lead when he would break Simon again in the next game setting up a breakpoint with a huge forehand winner and then the Frenchman would double fault to make it 5-2 for the Canadian.
He would have a great chance to serve out the match but the Frenchman wasn't going away quietly and would once again break back forcing the errors from his Canadian opponent.
At 5-3 the Canadian would once again have a chance to serve it out which he did when he would earn a match point with a great rally that he finished with a cross-court winner. He would win the match when Simon would send a ball into the net.
Shapovalov is through to round two where he will face Roberto Carballés Baena who earlier in the day beat American Steve Johnson.