Now, after a 10-year and 19-match losing streak against his fellow Yorkshireman, 33-year-old Willstrop can finally lose that millstone from around his neck, coming from behind to seal victory over the fellow former world No 1 in the second round of the JP Morgan Tournament of Champions, the traditional curtain-raiser to the second half of the season on the PSA Men’s World Tour.
It was, as you would rightly expect after such a long run in the losing column, far from easy. Willstrop prevailing in a gruelling 73-minute 11-6, 7-11, 5-11, 11-7, 11-4 victory at the Big Apple’s Grand Central Terminal.
The pair had met for the 34th time last month when Matthew scored an impressive straight-games win in the final of the British Grand Prix in Manchester. But under the chandeliers of the Vanderbilt Hall Willstrop could finally savour victory, taking the opener and then recovering from going 2-1 down in games to complete his first victory over Matthew since the 2007 English Open Final.
“It’s taken me a long time to notch that win against him, so I’m pleased,” said Willstrop. “Last month I didn’t play well against him and I was more disappointed with the performance than the result. He’s taken me out so many times that my goal is just to play well.
“I think the squash here was as good as it has ever been between us and we both played some very accurate stuff. I know what I’m capable of and I’ve been trying to work out the way to break him down for a long time. Today I did just enough to come through.
“And the best thing is I get to play here once again because I love being here at this event. To be out there and performing well in a good game of squash, it’s just brilliant.”
Willstrop admitted that he had found his losing streak against Matthew over the last few years tough to deal with at times, but admitted his victory on Sunday gave him the belief that he could deal with any opponent coming his way over the next few days.
“There’s no one better in tough spells, he’s incredibly strong and has a way of getting stronger when he’s behind,” added Willstrop. “Today in the fifth I had to make sure I didn’t get complacent, because he’s taught me enough times that I can’t afford to be.
“It’s been tough over the years. His game makes it very hard for me. There’s a lot of baggage associated with it as people talk about the rivalry, but it’s been a big run for him and to be honest I don’t think it has been a rivalry for the past few years because he has consistently beaten me.
“But if I can cope with his level I know I can beat any of the players in the draw. If I can keep my level high, stay injury free and have everything come together, who knows. But there’s a training session tomorrow to get through before thinking about anything else.”
While clearly disappointed to go out at such an early stage, Matthew admitted he always felt this day would come.
“He’s a class player and we’ve played some massive matches, so that win was coming some day,” he said. “He’s too good a player to have a record like that.
“He deserved it – even when I was 2-1 up I didn’t feel like I was on top. He was the aggressor today and I felt like I was chasing it.
“A few more matches in his legs could have made it a different story but I’ll learn from it and go back to the drawing board now to try and come back strong for the rest of the season.”