Pools sit fourth in the National League table with two games remaining and will be taking part in the promotion play-offs come June as they look to make a Football League return.
But in order to secure a top three place and a home play-off semi-final, they can’t afford to drop any points in their remaining matches against Sutton United and Weymouth.
It’s a high pressure situation for Challinor and his players to be in, but the Pools boss wouldn’t have it any other way.
“It’s going to be a mental test mainly because you know the margin for error is becoming less and less,” he told The Mail.
“We’re now looking at season defining games so there’s always going to be that pressure but if you want to get far in this game you need to be able to play under pressure and handle it.
"I can guarantee you the pressure we’re experiencing is a much, much better pressure than sitting at the bottom of the table, well maybe not this year, but sitting at the bottom knowing that you’ve got to win a game to stay in the league.”
Pools know that bottom of the table pressure all too well. But this season has been different and for the first time in 14 years, the club has a serious shot at promotion.
And regardless of what happens between now and the end of the season, Challinor has backed his Pools players to learn from the experience and come back stronger.
"The type of pressure we’ve put ourselves under is a great one and regardless of what happens, we’ll be better from this experience,” he added.
"In victory or defeat, sometimes defeat can hurt in such a way that it prepares you much better for next time.
"It’s a great experience and they’re ones that you wouldn’t change and ones that have huge opportunities for someone to be a hero.
"It’s a group of players who have the opportunity to take this football club back to where it has been previously and that’s what we all want.”