Today, the Blades go to Tottenham Hotspur looking down in the table on their exalted opponents. While the hosts have struggled to find their form all year, the visitors have made a fast start to the new campaign.
Fleck’s goal against Burnley last week secured an impressive 3-0 win which moved his newly-promoted team up to sixth in the Premier League. Spurs are slumming it in 11th.
Nobody expects either to be in their present position in May, but that United should be there now is no mean achievement for a side which in the summer of 2016 was preparing for a sixth consecutive League One campaign having just added Fleck to the squad.
This was not a Premier League-quality player taking two steps down in return for a big pot of cash. The talented Scot had not made it at Rangers, and 162 Coventry City starts pointed to a midfielder who had found his level in English football’s third tier. Now, like Chris Basham, Jack O’Connell and Billy Sharp, who became team-mates that summer and have remained so since, he can consider himself a bona fide top-flight footballer.
“It took me a few games to get to grips with it,” admits Fleck. “It was maybe a bit of a shock at the start.
“I well understand there’s going to be times in the season where we’re not in form but we’ve just got to keep working as hard as we can to keep it going.
“Over the last few years we’ve deserved to get promoted so we deserved to be in the league we’re in.”
Tottenham manager Mauricio Pochettino has spoken admiringly about the Blades’s “rugby team spirit” but if that was all there was to it, playing Premier League football would be a lot easier. Fleck has had to step up on so many levels since joining in the summer of 2016.
“When we were out in Spain when he was first here, John’s condition wasn’t what it is now,” Wilder recalls. “I just remember this kid gasping for breath. Now he just goes and goes.”
Again, though, there is more to it than that.
“I suppose I’d have to say it’s the best form of my career because of the level I’m playing at now and the division I’m in,” says Scotland international Fleck. “It’s all been down to hard work and my team-mates are playing very well at the moment, we’re working hard as a group.
“It’s just about being better at everything we do, in training and off-the-field stuff.
“In League One we seemed to have a lot of days off as a group, we can’t do that as much now. There will always be time to enjoy yourselves as a group but the standards have to be a little bit higher, as when the manager brings in new players. It’s just acclimatising to everything really to get better.
“We’re still all right to go out for a coffee but that spirit’s always been there since the manager came in. There are good characters, good people, and I suppose that’s something the manager looks at when he’s signing players, it’s not just how good they are technically, the character is a big thing here and we have great characters in the dressing room.
“I’m pretty quiet myself, to be honest. People like Sharpy, Jags (Phil Jagielka) and Bash (Basham), who’s been here for a while tend to lead that. They’re big characters who keep people on their toes.”
With a loan at crisis club Blackpool as well as his spell at turbulent Coventry, Fleck has had a tough footballing upbringing.
“There are difficult times but it’s about having the right mentality, especially when things aren’t going so well,” he explains. “You need to keep working hard, keep improving to get to the level where you want to be and I’ve had to do that, as have a lot of the squad here.
“When I was younger at Rangers pressure was there the whole time. Regardless of whether it was youth team or first team, it was about winning. You have to get used to that sort of mentality because losing games isn’t good enough. It’s just something you get used to, I don’t think it changes you. I’d had that since I was eight or nine-years-old. It’s just a mentality that grows in you and I think it’s stayed with me.”
Being made to work as hard for the success as Fleck and so many in the Bramall Lane dressing room have done must make it all the sweeter. Stop to bask in it, though, and it will soon come to an end.
“I certainly appreciate it more,” says 28-year-old Fleck.
“I can only speak for myself but it’s a great position to be in and we want to stay here for as long as we can. It’s about sticking together as a group and seeing if we can stay there this season especially.
“Maybe straight after a game you can enjoy the moment but soon your focus is on the next game already.
“If we don’t play to our best or work to our hardest, we can get beaten because we’ve not got the same quality of some of these top clubs.
“We’re sitting sixth but it doesn’t make much difference to us as a group.
“Since the start it’s always been our aim to stay in the division. If we keep working as hard as we can on the training ground and keep sticking together you don’t know where it might take you.
“But we know there are going to be difficult times ahead when we could lose two, three, four on the bounce and it’s how we react to that.”