The final against Liverpool is a great opportunity for Di Matteo - and no doubt a huge surprise too. Having been sacked by West Brom not much more than a year ago, the Italian is probably pinching himself constantly now he has an FA Cup final and a Champions League final to look forward to.
A great many managers go through their entire career without getting even close to such a stage. However, even if he does win either or both of these competitions, I don't think it will suddenly make him a great manager or the right long-term choice for Chelsea.
If somehow Di Matteo does mastermind a victory at Wembley and then again at Munich's Allianz Arena it may prove very difficult to get rid of him - particularly given the affection that Chelsea fans hold him in following his playing days with the club.
But realistically I think Chelsea will have to get somebody with more credibility for next season - someone who is capable of making tough decisions and breaking up the over-powerful dressing room that has proved such a burden to previous managers.
Winning the FA Cup alone will certainly not be enough to get Di Matteo the Chelsea job, so he should enjoy the Wembley experience while he can.
When Guus Hiddink won the FA Cup as Chelsea caretaker manager in 2009 there was a groundswell of support for him to get the job on a full-time basis - amongst, players, officials and the public - only for him to return to his role with the Russian national side.
I think it is a different situation under Di Matteo, even if certain players might want to keep him in as a kind of puppet. Is he the man to take them forward and make Chelsea capable of challenging for the Premier League next season? No chance.
He proved at West Brom that he wasn't up to it. He started well but when it got a bit tough he didn't know what to do next. If he going to embed himself and rebuild his managerial career, then I don't think Chelsea is the place to do it.
People point to an upturn in form under Di Matteo since replacing Andre Villas-Boas and the fact he has taken Chelsea to two cup finals but I just think the players now feel they are working under someone they can influence, which has resulted in some improved performances.
As far as I am concerned, certain players are still running that team and they are back playing in the manner that they did under Jose Mourinho. Di Matteo hasn't had much of a say in it in all honesty.
As for the likely outcome of the game, I just think Liverpool might have the luck on the day. This is a final between two sides who have had disappointing seasons in the Premier League but perhaps Liverpool will get the rub of the green.
Certainly they have had a terrible season under Kenny Dalglish and people are now living in this world where they are kidding themselves that winning two cups is a great season. I think that is a myth and it is an embarrassment to what Liverpool were as a club two or three decades ago. Liverpool have always been about winning leagues and winning European Cups.
Their football this season has also been poor and overly negative and if they do win the FA Cup they will enjoy the day, but the future still won't hold much as their league campaign has been absolutely shambolic.
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