The recently departed player-coach might have been a 35-year-old veteran when he arrived at the Proact, but Chesterfield still managed to give him plenty of new experiences.
A league winner’s medal, a Wembley appearance, a match-winner the day after the birth of his son and a wealth of coaching experience are what the PFA chairman will cherish in his post-Proact life.
Humphreys is still unsure where the next chapter of his career will take him.
But if it contains anywhere near the level of excitement that the last chapter contained, he’ll probably settle for that.
One of his four seasons with Town stands out and one day was particularly unforgettabe.
“Without a doubt winning the league on the last day of the season at the Proact, all the players being carried off the pitch on shoulders,” he said.
“For me personally thinking that summer when I did sign for Chesterfield that I wasn’t sure I was getting a club at all, to go in then and to play as many games as I did and to win the league.
“I had never had a winner’s medal, I’d got promoted a few times as a runner-up, so to finally get a winner’s medal was fantastic.
“The open top bus, things like that you don’t forget, those are highs you can’t forget in football.
“Finally playing at Wembley in a cup final, I hadn’t achieved that in my career so to do that in the same season was brilliant.
“My little boy was born, we won the league, I was made chairman of the PFA and I played at Wembley, so it was an amazing year.”
The 2013/14 League Two-title winning season featured a pair of rarities – two Humphreys goals.
He left the Proact having only ever scored three for the club, but one was incredibly special.
“There haven’t been many,” he laughed, when asked about his favourite.
“It’s so easy for me to pick though, the goal away at Oxford the season we won the league.
“My little boy was born on the Friday and I was unsure whether I would be able to play or not.
“Everything was fine, he was fine, my wife was fine.
“I went to the hospital in the morning and then my best mate drove me down to Oxford, Paul Cook said that was okay.
“I played, scored a goal from left-back that turned out to be the winner.
“You think could that ever happen, it happens to other people, but it happened to me that day.
“I was straight back to the hospital to see him and my wife.
“It was amazing. A tiring but amazing 24 hours.”
On the field he achieved championship glory and reached Wembley in the JPT final.
Off the field, Humphreys was given the chance to manage the reserves and even had a breif spell in charge of the first team, in the wake of Danny Wilson’s departure.
He’s proud of the coaching work he completed at Chesterfield and feels he’s gained a lot from it.
“Working with the reserves was just a fantastic experience, working with that mix of senior players who need games, handling them coming back from injury, working with Mark Smith and Dylan Kerr with the youth players,” he said.
“What’s been great for the whole club is that we’ve seen some progressions as well, from the youth team with the likes of Joe and Charlie.
“Young lads like Tendayi (Darikwa, Burnley) who I spoke a lot with, I’ve always thought it important for senior players to do that.
“I had it when I was a kid at Sheffield Wednesday, I had a lot of senior players who were excellent at trying to motivate and get you to be the best you could be.
“It’s a tough profession and I’m so pleased those young lads got the opportunity to play at the end of last season.
“Laurence (Maguire) now has his new contract, there’s a lot of good things that have come at the club.
“Taking those two first two games, winning the league game that was so important at the time, it was a great experience and I thoroughly enjoyed it.”
Humphreys is tight lipped on his immediate future or even what avenue he might take.
He hopes there are good things in store for the club he’s just departed, though.
“All the managers I’ve played under have been brilliant.
“Gary (Caldwell) is top class, an excellent manager, a good coach, the same with Steve (Eyre) and Dukey (Matt Duke).
“I enjoyed my time there, I wish them every success.”