In late 2008 a young and innocent Will Sharp tossed aside his well-worn copy of FIFA 09 in favour of Football Manager 2009, eager to test himself against the juggernauts of managerial simulation. What he envisaged being a simple transference of skills and a continued domination of the digital football world soon descended into chaos as he found himself unable to even compete. Unsuccessful save after unsuccessful save cut short, the intervals between hopeful attempts grew exponentially until eventually, he stopped logging on altogether. Truly vanquished, he vowed never to attempt to conquer Football Manager again. Until now.

Chapter 17: Voyage To The Middle Of The League

Captain’s Log, 22 October. “There has been a lot of speculation this week linking you with the vacant Brentford post. Are you interested in the job?"

This is the question put to me by MailOnline’s Brett Wilson after my Wednesday team put three past Preston, without reply, continuing our stroll up the table before settling temporarily in fifth place.

The first question bearing even a hint of inquisitiveness; the first meagre attempt at extracting even a modicum of exclusive insight into the incomparable existence of me, Will Sharp, Sheffield Wednesday manager, after the latest of so many vintage attacking displays, and the opportunity is taken only to ask if I am interested in taking over at 22nd place Brentford.

I chuckle, scanning the room from side to side, smiling and sharing in the nervous laughter that soon joins my own, before my face slumps into an offended glare. Suddenly I'm launching a saucer of Viennese swirls across the room in the direction of the correspondent in question while spitting feathers. "BRENTFORD? AM I INTERESTED IN THE JOB AT BRENTFORD?"

The next thing I know I'm at home on the sofa, watching Bargain Hunt with Oscar beside me, and I have 67 text messages on my phone. The only one I bother to read says just "Good game today, boss." It's from Conor Hourihane, scorer of two of today’s goals. I message him back a string of emojis. Football, football, fire, fire, fire, flexed bicep, flexed bicep, smiling face with heart-shaped eyes. He doesn't reply. I fall asleep before bothering to find my bed.

25 October rolls around and it's time for us to welcome Premier League pretenders Aston Villa back to Hillsborough with a place in the EFL Cup quarter-finals on the line. More importantly, the evening presents an opportunity for me to triumph over my old rival Karl Robinson. Some may remember him as the man who stole from me a Manager of the Month award last season, on account of him having an "objectively better record during the month" or some other bureaucratic bullshit.

I tell each of my staff to tell their mates to feel free to tell any of their mates who may know Karl Robinson to tell him I'll be starting with a highly rotated line-up. I put added emphasis on the word experimental and I make sure to sell the line with a few nonchalant shrugs while pretending to forget the competition's name. "It's only the Worthingto—Coca Co—whatever the cup is, lads." Then I send out our strongest XI.

Poor old Karl. Sitting there on the away bench, with his pals and his Manager of the Month trophy, all forlorn; powerless to prevent his team from being decimated. Matias in at the far post. Bang. Jones with a penalty. Bang. Jones again, this time deflected, from range. Bang. João in off the bar. Bang. Then Villa grab a consolation; disallowed, Solanke offside. As good as another bang. Full time is met by rapturous Wednesday applause.

“Robinson.” I nod. “Sharp.” He nods. We go our separate ways. Me; onwards toward the quarter-finals with a jubilant team, him; home for a microwave spaghetti carbonara for one. God, that was sweet. Less sweet, though, was the draw that followed. The EFL Cup quarter-finals will take us to Old Trafford.

But before our EFL Cup adventure continues we must return to urgent matters in the league, as we’re required to do battle with Wolverhampton Wanderers on an occasion which proposes an interesting and almost philosophical contemplation: if a Keiran Westwood flaps at a long-range effort and nobody is there to be surprised, does he still concede from 35 yards? The answer is yes, he does. And that's that for the Wolves game. 1-0. I don't even remember us having a shot. Funny how quickly unbridled joy can descend into face-achingly typical disappointment, isn’t it? Hilarious, that. Never gets old.

The Wolves debacle is followed swiftly by a tie against Burton Albion, who are busy making a bit of a mess of their second attempted Championship survival mission, and it's a mess of a goal that gives us the early advantage. Matias collects the ball inside the area, after both sides put together a cracking impression of a pinball machine, before Matias assumes the role of the flipper, firing the ball into the bottom corner, courtesy of a huge deflection off the knee of Federico ‘Bumper’ Macheda, leaving the Burton keeper stranded. And that's that for the Burton game. Just two more games and then it's back to the cup. The good old, lovely, winnable EFL Cup.

Before our game with Huddersfield, our ever-present left-back Neil Taylor is ruled out for 5-6 weeks with a sprained ankle, which ultimately works in his favour as it helps him to hobble out the way of the incoming shitstorm.

With time enough between now and the quarter-final, I opt to stick with our strongest XI but the decision pays me no recompense as we’re well beaten by the Terriers. The fact the two sides were parted by just a single goal did us a world of favours. Almost made us look like challengers. Hoop-Dogg ended his own personal dry spell, which was promising, but goals from Scannell and Wells were enough to see us off.

I make a flurry of changes for the following fixture against Blackburn, partly because those entrusted with seeing off fourth-placed Huddersfield did themselves no favours with their recent performance, and also because I’ve no choice but to rest players for the United fixture in a few days time. I simply have to prioritise the cup. I know full well fans may want promotion—who doesn't?—but promotion only gets us Premier League. An EFL Cup win gets us Europa League. Most of these fans have never been to Europa.

The ensuing two fixtures prove to be transformative, but unfortunately not in the same way, a caterpillar metamorphoses into a beautiful butterfly, a bud blossoms into a flower or funky smelling milk does whatever milk does to become cheese. Instead, it's much in the way a team dreaming of an early trip to Wembley are rudely awoken by the feeling of wet sheets and the unmistakable smell of piss.

The second stringers muster a 2-1 win over bottom half Blackburn, thanks to a double from João, and I’m left with a bit of a selection headache. Do I opt for the usual suspects, so often reliable but who cocked up against Huddersfield, or those more used to the sidelines who seized their moment in the spotlight against the comparatively lacklustre Blackburn? This is United we’re talking about.

In the end, I go with a blend of the two. Enough familiar faces to ensure we keep our cohesion, but with a few key tweaks that should endeavour to freshen things up and surprise the Premier League, big boys. We did Chelsea, we can do United. Another giant killing, fellas? DO WE FANCY IT?

Nope. We turn up, more than ready to lock horns with the Red Devils, but, unbeknownst to us, the evening has been earmarked for another live recording of The Rashford Show, during which we're unfortunately scripted to be bent over Jose Mourinho's knee and given three firm reminders of our place in life.

I attempt to make some kind of amendment to the evening's scheduling with my pre-game team talk but it's too late. Evidently, once the script has been given the green light you can't change it, so we lose 3-0 and depart the competition with all the grace of a balloon slowly losing air as it flits pointlessly around the room before landing limp on a lampshade. There is nothing I can say to ease the pain for the lads. We really wanted this one.

I attempt to put the disappointment behind me, tell the lads to refocus, we’ve still got the league and the FA Cup to fight for. Nobody likes the EFL Cup anyway. It’s crap. But before the week is up one final, agonisingly inevitable insult remains to be slipped under my bedroom door for me to discover and ruin my day: Tim Sherwood is named Brentford manager.

I didn't even want the job, really, I didn't. But... Tim? A month after they reportedly wanted me, they hire Tim? Things are worse than I thought.

Catch the end of Season 1 (and other posts) here. The start of season 2 is here with chapter 13 and here's Chapter 14. Catch up on Chapter 15 here. Chapter 16.

By Will Sharp. Chapter 18 coming next Thursday, June 8th. Header image credit goes fully to John Lord.