An under-pressure Chelsea manager has to negotiate a tough Champions League fixture away in Italy following a difficult run of just two wins in seven games. Tasked with implementing a new progressive style, the previous few weeks have seen him suffer as he tries to deliver what his owner demands. A clean break with the past proves hard; evolving the team's ingrained approach is an endeavour beset by pitfalls.
Rumours he may ignore big reputations when selecting his starting XI are proved correct but a bold tactical move backfires when his side concede three and are left humiliated, the classy Italians exposing the limitations inherent in the new approach - one mandated by the Russian who runs the boardroom and still in its relative infancy.
Only hours after the damaging loss, with Chelsea one game from elimination or redemption, reports emerge that Rafa Benitez has already been sounded out to replace our poor protagonist. Of course, he is only likely to be a stop-gap measure, with Pep Guardiola the real prize when he becomes available at the end of the season. Another Chelsea manager looks destined for the chop.
If Roberto Di Matteo has a nagging sense of déjà vu following last night's 3-0 loss to Juventus, it's probably because he witnessed a near identical scenario as right-hand man to Andre Villas-Boas last season when Chelsea were defeated 3-1 at Napoli. The similarities really are quite eerie.
As history appears doomed to repeat itself, and Roman Abramovich prepares to wield yet another P45, it is worth asking just what Chelsea may hope to achieve if they dispose of Di Matteo - a move that ED would argue is hugely unjust.
In the short term the dismissal of Villas-Boas last season brought Chelsea the European Cup - the finest night in the club's history, overseen by a certain Roberto Di Matteo of course. But this triumph was the last flicker of an old Chelsea: negative and suffocating. It did not mean that Villas-Boas was wrong to try and give the squad a more youthful, progressive slant as instructed by Abramovich, even if his execution was clumsy and his dismissal ultimately vindicated.
Instead, the process of renewal was accelerated in the summer when Abramovich dug deep for Oscar and Eden Hazard, among others. It signalled a new conception of football at Stamford Bridge.
At the start of this season it appears Di Matteo was given a brief to shed the shackles of the past and implement a new attacking style. It worked well initially as Chelsea won seven of their first eight league games but the club's young players, quite understandably, have suffered a dip of late. Completely changing the approach of a side is not easy work, not when the previous approach proved so successful. Just ask AVB about his attempts to ask John Terry to play a high line.
Rather ironically given the whims of the club's owner, elements of Chelsea's squad are hard wired to resist change. John Obi Mikel demonstrated as much in a brutally honest interview with ITV.
He said last night: "I think the way we play sometimes, we're very good going forward, but when you lose the ball you need to defend, and you can't do that with six men, you need it to be the whole team. It has to be the team, and that is how we were successful last year.
"People say we didn't play attractive football, yes, but we won trophies. This year we want to play attractive football, and this is what we get. We don't want to be a team that plays attractive football and doesn't win games.
"We have to have that [foundation]. This has been the way we play. This is the way Chelsea play: we are very tough physically, we are very tough when we lose the ball. Now we just don't seem to do that and it is very easy [for other teams]. When we don't have the ball now it's a nightmare."
There's no doubt that under Di Matteo Chelsea have a soft centre, yet surely this is a symptom of the change in style that we are told Abramovich has desired for so long. A balance can be struck between the florid play of Hazard, Oscar and Mata and a sound defensive strategy, if only a manager is given time to find it. Let Di Matteo try and iron out the kinks - surely he has deserved that much after winning the FA Cup and European Cup, making Chelsea more competitive in the league and spending half his working hours having to deal with racism controversy after racism controversy, while all the time his master stays mute.
And as for Chelsea's problems up front, they are the result of the owner's decision to foist £50 million Fernando Torres on a team that didn't need him, not when they had Didier Drogba in situ. Clearly having learned nothing from the disaster that was Andriy Shevchenko, Chelsea wasted extreme amounts of money on a trophy face that didn't fit. And while Di Matteo may be criticised for using Hazard up front against Juventus, he had little choice. Hazard might be a false nine but you'd struggle to argue that Torres is a genuine striker any more. Abramovich's star acquisition is a burden to his team.
You can't really fault the owner's desire for more attacking players, just as you couldn't fault the mandate he gave Villas-Boas to rejuvenate an elderly squad. But when things get tough, the answer isn't to rip things up and start again. Admittedly, doing so brought Chelsea the biggest prize in football last season, but did it really push them forward as a club? No, they still needed Di Matteo to take on that project.
If Guardiola is the end game this summer then fair enough. ED wouldn't blame Abramovich if he donated half of his assets to charity if it meant getting the most in demand coach in the world, and possibly in the history of football. But what sense would it make to sack Di Matteo now to bring in another stop-gap measure? A club legend like the Italian deserves better.
Chelsea are four points off top in the Premier League and progression from a very tough Champions League group is not yet beyond them. This is not a sackable offence. But as previous Chelsea managers have found, and Guardiola may yet in future, nothing can insulate against Abramovich allowing history to repeat itself once more.
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QUOTE OF THE DAY: "After my first training session with Rangers, I went quietly into the shower when I noticed a foul smell coming from my kit. I looked more closely at my pants and I noticed there was something heavy inside. Paul Gascoigne had pooed in my pants! He's crazy, end of story. It's his way of being. Then I had to go home without any pants on." - Gennaro Gattuso. What else do you need to know?
FOREIGN VIEW: "I don't know if Shakhtar are bandits, but some of their players, bosses and coaches are without morals." - Nordsjaelland coach Kasper Hjulmand reflects on one of the most controversial periods of play in Champions League history. In an astonishing sequence, Shakhtar's Willian sportingly attempted to play a drop ball back to the Nordsjaelland keeper following a stoppage in play. However, as the home defence stood aside, striker Luiz Adriano suddenly decided he would round the keeper and score.
An incensed Nordsjaelland were then allowed to dribble forward unopposed from the kick-off as Shakhtar attempted to allow them to score, only for Taras Stepanenko to disposses Nicolai Stokholm. The Nordsjaelland captain said after a stormy encounter that Shakhtar won 5-2: "Their attacker didn't get it. I looked down at my armband, and there's something about respect — it has to be said we didn't see much of that."
COMING UP: Another busy night in the Champions League as Arsenal play host to Montpellier and Manchester City hope for a miracle against Real Madrid in the pick of the 7.45pm kick-offs. The action gets underway at 5pm though as Zenit host Malaga in what should be an entertaining contest. Prior to all that, Jim White files his latest blog and we put a rising star at Reading Under the Microscope.