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Should Stockport reign victorious on Sunday, Challinor would write himself into the club's history books.
County have never won the EFL Trophy but have previously come up short on two occasions in successive seasons - in 1992 and 1993.
"When this competition starts, maybe the first thought isn't getting to a Wembley final, but the further you progress that thing certainly enters your thinking," Challinor told BBC Radio Manchester.
"As much as we've been successful over the past few years, the opportunity to go and play at the home of English football on a national stage in terms of what the competition brings is one that we have to look forward to."
Challinor is the first manager in Stockport's history to take them to Wembley on more than one occasion.
He hopes, however, that their second trip to the national stadium is more prosperous than the last time, when they were beaten by Carlisle United on penalties in the 2023 League Two play-off final.
"Wembley never gets old or is something you don't want to experience. I went to the old Wembley as a player and I've gone to the new one four times as a manager," Challinor said.
"I'll never lose sight of the fact that I am really lucky to do that. To go back there with this club is great and shows that we've been progressing and moving forward.
"The last one ended in disappointment and we'll go to right some wrongs, if you like. It's a brilliant occasion but you have to embrace it."
Challinor's managerial career is at a different point to that of Wilshere, who is still at the beginning of his coaching journey.
Despite this, the pair know each other having completed their coaching credentials together and Challinor says his counterpart knows what is expected of him.
"I know Jack, I did my Pro Licence with him. When players come down from the Championship and you don't have alignment, it takes you a while to get going and that's probably been the case. But they've had good runs throughout the season and they've got stacks of quality within their team," Challinor said.
"We know it'll be really tough. We know we'll be outnumbered in terms of supporters, but our supporters will certainly make themselves heard."
