Chesterfield had planned to send the striker out to get games with the National League club, but the 20-year-old prefers to see what’s available to him in the January transfer window.
Wilson said the move would have helped Simons get closer to a place in the first team.
“There were plans to send him but he refused to go. York City wanted to take him but he wanted to see what happens in January,” said the manager.
“When you’ve got opportunities to go and play National League level, it’s important.
“That would have been as good an education as anything and a big help to throw down a marker to me for the first team. He didn’t want to go and that’s disappointing from my point of view.”
The manager’s words suggest Simons’ future at the Proact might not be so secure.
And it seems unlikely he’ll find himself back in the first team any time soon, although Wilson’s attacking options are limited with Connor Wilkinson out for two to three months, Kristian Dennis struggling with a calf injury and a question mark remaining over the fitness of Ched Evans.
Wilson said: “He needs to go out and play games and I would let him go.
“Rai has not played, he’s had a hamstring injury, he’s played something like one game in 10 weeks and that’s not enough.”
Simons joined the Spireites from non-league Ilkeston in April 2015.
Last season the five-times capped Bermuda international played 22 times for Town, scoring five goals.