The 15th seed immediately put Simon under pressure. After holding his opening service game with ease, Monfils then won the baseline rally with his French teammate sending a backhand long to bring up a break point chance at 30-40. The breakpoint was quickly snuffed out but Monfils would bring up a second just moments later.
The 30-year-old did get the break with Simon putting a forehand straight into the net. He then followed this up by consolidating to 30 for a comfortable 0-3 lead. Things only got better for Monfils throughout the set. Just a game later, he would take a love-40 lead. Simon managed to take the game to deuce, saving triple break points and a fourth at advantage.
Eventually, after piling on the pressure, the world number 16 broke for the second time with Simon once again piling on the unforced error. Another easy hold of serve from Monfils allowed him to take a 0-5 lead. Now with the set just under 30 minutes, the 32-year-old found himself serving to stay in the set.
But again, it was Monfils who dominated the game, winning three straight points and bringing up a break/set point at 30-40 with Simon over doing a backhand down the line. A poor second serve allowed Monfils to attack and hit a perfect backhand winner to seal the set 0-6.
Simon bounces back
After a poor first set, the second was much better for Simon. With a couple of rallies going his way, double break points then went in his favor after a poor dropshot allowed Simon to venture towards the net, return the shot and finish with an overhead winner. First time of asking, Simon broke the Monfils serve for the very first time, which he consolidated to turn the match in his favor at 2-0.
This time, it was the turn of Monfils to produce the unforced errors at a costly time, allowing his French compatriot to bring up more break points, two of them. The 30-year-old could only save one with Simon going up a double break lead by turning defense into attack and forcing an unforced error.
Looking to avoid a bagel, Monfils started dictating the rallies and pushing Simon further back as two break back points went on offer. Simon then responded spectacularly by denying the 15th seed and going even further infront at 4-0.
Up love-40 in the very next game, Simon pegged his French opposition back by winning four points on the bounce to take the game to deuce. Starting the point on the front foot, Simon unleashed a backhand winner to take a 5-0 lead. The 32nd seed won the set, 6-0 via an unforced error as the match reached its hour mark.
Simon advances via tiebreaker
With the momentum fully on Simon's side following the second set, he failed to make that count. In fact, Monfils wrestled that momentum and earned a break point in the second game at advantage after holding serve previous. He needed just the one chance to put away the point with Simon netting.
Monfils consolidated and once again the match had swung in his favor, 0-3. Simon eventually held serve to get on the scoreboard and after a second bagel in this match. More rallies were to come in this set, with both players going hammer and tongue at each other. Behind in the scoreline at 5-2, Simon was suddenly serving to stay in the tournament.
30-all, the 30-year-old was gifted a break/match point with Simon firing a double fault. He made amends and denied Monfils to send the game to deuce. The 15th seed would have another crack at finishing off the match but a resilient Simon once again denied Monfils and held serve.
Simon then found inspiration and with his Davis Cup teammate serving for the match, he went love-40 ahead and broke back immediately before sending the match to a tiebreaker. The 32-year-old ran away with the breaker, going 6-0 up. After just over two hours, Simon finally put the match to bed and advanced.