He played in 485 career games in total, experiencing the highs of the Premier League, the lows of League One and then life on the other side of the world in the Australian A-League.
But, Nick Montgomery admits, one sticks out in his mind.
“My first Sheffield derby, at Hillsborough,” the now-retired 35-year-old smiles.
“I was 18 and it was only my third start for Sheffield United, and the first competitive derby in almost seven years.
“It was a League Cup tie and the build-up started from the moment the draw was made. I remember driving from Bramall Lane to Hillsborough; going past all the Blades pubs and the fans cheering and singing, and then the Wednesday pubs shouting abuse.
“For me, it was surreal. I remember walking through the abuse around the players’ entrance, and hearing the vibrations of the walls in the dressing room.
“Apart from the other derbies, I never experienced that again in my career. I can still remember the game, too, and the referee stopping the game early on as two fans spilled onto the pitch and having a scrap.
“Wednesday scored first but I set up Michael Brown for our equaliser; a sweeping ball behind their back four which Browny slotted past Kevin Pressman. The whole place went crazy!
“After that, I should have scored - to this day, I don’t know how Pressman got his fingertips to the ball to push it onto the post - and Marcus Bent hit the bar from about five yards out, before Wednesday scored an extra-time goal to win it.
“The memory of losing that day was horrible, of course. But that day, I knew what it meant to be a Blade.”
Montgomery, who played over 350 times for United before signing for A-League side Central Coast Mariners, announced his retirement from professional football back in May, accepting an off-field role with the Mariners.
Born just under 30 miles away in Leeds, Montgomery called time on his career just over 10,500 away on Australia’s Central Coast. But for most of the time in between, his heart remained with United.
There were other big games, too; despite dividing many Blades fans, he was good enough to play for them in League Cup and FA Cup semi-finals, experience two Championship play-off finals and make 26 appearances in the Premier League season of 2006/07.
“But still, playing against Wednesday is normally the first thing people ask me about,” he added.
“Which I understand, as it’s one of the biggest derbies in football. The players feel it hard as well as the fans; I actually saw some players over the years pull out with injuries just before a Sheffield derby, and I think the pressure of playing in them could be too much for some.
“The expectation from the fans is huge, and I always struggled to sleep before these games because of the pressure on my shoulders, even as a young player.
“Then, the older I got, the more pressure I felt because I felt it was my job to ensure that the new players knew exactly what this game means, and what they should expect.
“As a player, a win can mean you can walk around with your head held high for a few weeks and a loss almost makes you want to go into hiding.
“I was involved in many derbies in the end, and to have them back is massive for the city. I’m lucky in that I didn’t experience too many defeats against Wednesday, and I can’t wait to watch them both on TV.”
This article and more feature in a 16-page special supplement inside Saturday’s Star, previewing Sunday’s big derby clash. It includes interviews with figures from each club, past and present, offering their insight into derby day.