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.

Catch the end of Season 1 (and other posts) here. The start of season 2 is here with chapter 13.

Chapter 14: Around The Form Guide In Eighty Days

Captain's Log, 6 August. Well if it isn't my old friend; the dream-killing, confidence-sapping, weekend-ruining, gut-punting stoppage time goal to lose the game.

Despite more than matching Swansea stride for stride during the game, Conor Hourihane regretfully besmirches his fine competitive debut by relinquishing possession far too easily in the middle of the park. From the turnover the ball is switched out wide to Tabanou, who wastes no time in whipping it into Barrow, standing painfully untroubled by markers, or even casual observers, in the box and takes it upon himself to fire the ball beyond Westwood to give Swansea a 90th-minute lead and with it all three points.

Should we have won, as I anticipated us doing following our faultless pre-season, I'd have given each of the lads the matching bracelets I'd secretly beaded while we were on our travels in pre-season. Each of them reads 'PORTUGALLNIGHTLONG', spelled in tiny engraved cubes; to remind them of the evening we spent together on the Praia da Marinha listening to Lionel Richie. God, I remember those days like they were just weeks ago.

But that can wait. The kind of performance they put in today warrants no reward whatsoever, let alone the heartfelt handmade mementoes I had waiting for them. It was even on TV for Oscar’s sake.

Still, I put too much time and effort and love into the bracelets not to give them to the boys at some point. Maybe I’ll repurpose them at Christmas.

Luckily for the squad, they've an opportunity to bounce back almost immediately, away to Shrewsbury, in our first EFL Cup tie of the season.

A little over five minutes in and what I see before me almost tips me over the edge. As Shrewsbury strike from some 25 yards out to take a surprise lead I’m just about ready to run to my office, grab the satchel from my locker, pull out the bracelets and stamp them into the carpet then and there. But we soon battle our way back level, and the bracelets are safe for another week, and come the end of the match it is our turn to snatch a late winner as Izzy Brown enters the fray and scores the game's decider with 91 minutes on the clock.

Despite what I may have said in the past about late goals, actually, as Brown's helped me to realise, I'm really quite a big advocate of them.

On 10 August the EFL Cup second round draw takes place and grants us an away trip to Cambridge. I can't pretend to know a great deal about our upcoming lower league opponents but they have the letters CU boldly emblazoned front and centre on their badge so I can only assume we're playing them next Tuesday. Also the brief fact file I received on the club informed me, under the subheading entitled ‘stadium surface’, that they do in fact play on grass, so that's a big help.

With the arrival of the following Saturday comes a trip to stadium:mk to take on MK Dons; our second shot at earning our first win of the Championship season. By the time we're done in Milton Keynes I'm about ready to book the open-top bus for May.

Four different scorers in João, Forestieri, Hourihane, and Jones, a faultless shutout of the MK Dons’ arsenal worthy of an all-Italian five-man defence, and a complete performance from every member of the team. The lowest rating on the day goes to Kieren Westwood in the Wednesday goal; his not-particularly-low 7.1 presumably a direct result of his spending the majority of the game propped against the near post, wrestling with a number puzzle. “Confident in goal but lacked ideas when solving his sudoku.”

After his role in the 4-0 victory, the plaudits pour in from the online fan base in the direction of our man of the match, João. "You'll do well to see better than João," says Mia O'Sullivan. "João very good today, good decision to get him on the back of my shirt," says Bradley King. "If I had a wife I’d love her less than you," I tell him.

On the eve of our game against Brighton, news reaches the club of João's presence in the Championship Team of the Week, and he is joined by fellow Wednesday teammates Hunt, Hutchinson, Taylor and Forestieri. I tell the lads that in next week's TotW I want all eleven.

In our third league outing, we battle to a 2-2 draw with Brighton. Having twice taken the lead—first through an early Marco Matias strike and the second courtesy of João's finishing off a slick move that comfortably stakes his claim for Goal of the Month—it is frustrating not to pick up the win. But credit to Tomer Hemed for his finely taken brace, pegging us back on both occasions with excellent first-time finishes. Come January, a bid from the Wednesday hierarchy could well be on its way to Brighton. That or a horrible bloke with a mallet.

Before the following game with Birmingham, we're able to successfully complete the signing of Jamaican defender Michael Hector from Chelsea, for a little over £3 million, who slots straight in alongside Sasso at centre back.

I’m informed the fans are encouraged by the addition of a player of Hector's ability but are concerned we now have too many centre backs. But fear not my little Owl lovers, by my calculations, with the number of illogical outgoing loans I’ll willingly sanction and unforeseen injuries we’ll inevitably face between now and May, I’m certain we’re around par.

In the lead up to our trip to Birmingham, I hand Hector the number 92 shirt; 1992 being the year of his birth. This is something I've seen the abnormally-high-shirt-number-loving Italians do for years, and they wrote the defensive blueprints, so my motivation is simple.

Against the Blues, we're able to mark Man of the Match Hector's excellent debut with an expertly kept clean sheet, which we supplement with a finely taken goal to give us the win. Jones does the business, as he so often does, firing past the stranded Kuszczak from outside of the box and we’re grateful for a much-needed victory.

This time last year we exited EFL Cup at this very stage so I’m eager to right last season’s wrongs but this doesn’t stop me preparing for our encounter away at Cambridge by making nine changes to the line-up. To my delight, the XI picked ostensibly lacks no cohesion and dispatches our inferior opponents with ease. Goals from Brown and Abdi secure the result and ensure our safe passage to the third round where, as we find out in the following evening’s draw, we'll welcome to Hillsborough the might of Chelsea.

With the likes of Peterborough, Scunthorpe, and Wycombe still in the competition, it is frustrating to be handed such an early tussle with one of the English giants. But it does set up the possibility of a devilish little narrative involving our newest signing. Did I hear somebody say Michael Hector with the late winner?

Catch the end of Season 1 (and other posts) here. The start of season 2 is here with chapter 13.

By Will Sharp. Chapter 14 coming next Thursday, May 18th. Header image credit goes fully to John Lord.