It ruled him out of the remainder of the campaign - as Spurs were fighting to stay in the Premier League - and this summer’s World Cup, where he would have played with the Netherlands.
Roberto De Zerbi did oversee top-flight survival for the north Londoners, which came on the final day of the season, but the Dutch were eliminated early in North America, as they were beaten on penalties by Morocco in the first knockout round.
Now, speaking to The Sports Agents podcast, Simons has given an update on his fitness as pre-season gets underway.
“When they tell you how long this injury is, and for me the first two days were really hard. But after that, I told myself, don’t put the pressure really, really high on myself, and I'm seeing improvement every day, and that's something that makes me really happy.”
The ligament rupture meant that Simons missed what would have been his second World Cup of his career, having featured in a bit-part role in Qatar four years ago.
“This World Cup was a little bit different because I [felt that I] really could help the team to achieve the goal,” he explained.
Looking back at sustaining the injury at Molineux, Simons said that he was grateful to be able to do menial tasks after what is seen as the most devastating injury elite athletes can suffer.
“I have to be happy just walking again, going to the toilet and even having a drink with my family. So, that was something that really hit into my head.”
He is still unlikely to feature for Spurs this calendar year, with his return expected for 2027.