Two successive defeats, against Newcastle United and Liverpool, have ensured we will finish in our lowest league position since 2002, but the Italian was both honest and forthright in his assessment of where we've gone wrong.
'It's very simple, we just haven't won enough games to get the points needed to finish in the top four,' he says.
'Normally it's a combination of the two, when you don't get the wins you probably haven't scored enough and you've conceded too many goals, it's about finding the right balance between those things, but it's certainly proven a difficult season for us.'
Nobody would deny that it's been a dramatic season in west London. After replacing the outgoing Carlo Ancelotti, Andre Villas-Boas was dismissed at the beginning of March, following a dreadful sequence of results which saw our title assault collapse and our Champions League aspirations hanging by a thread.
Di Matteo was tasked with replacing the Portuguese, and the former Blues midfielder has turned things around dramatically by already securing the FA Cup and bringing us to a mere 90 minutes away from Champions League glory.
Unsurprisingly, the build-up to tomorrow's clash with Steve Kean's side, who were relegated to the Championship last Monday following a 1-0 home defeat against Wigan Athletic, has been dominated by talk of next Saturday's clash with Bayern Munich in Germany, and the interim first team coach admits he is leaving no stone unturned in preparation for what is arguably the biggest game in the club's history.
'All the time I have, I will dedicate myself to preparation for Bayern Munich,' he says. 'I watch many games, I will go and watch them on Saturday night in the German Cup Final and analyse their patterns of play.
'I've seen them play before, I saw the two semi-finals and also watched them in the group stages. I know the game is in Munich but the stadium will be split; it's a one-off game, we know how they can play, I've seen them play away and at home, so we'll see.'
The last couple of months, ever since Di Matteo was handed the reins, have been a whirlwind of crucial matches virtually every three days, as we've attempted to battle successfully across three fronts.
Regardless of what happens in Munich, Di Matteo has emerged from the second half of the season with a great deal of credit for the way in which he he's steadied a ship that was veering way off course at one point.
With every impressive result, the calls for Di Matteo to be handed the role on a permanent basis gather momentum. Supporters have made their feelings abundantly clear in recent weeks as to what they believe should be the next step, but the man himself is simply taking it game by game.
'At the moment I'm not thinking about that, when it's the right time to think about those issues or decisions I'll do that,' he says.
'At the end of the season, or after the last game, the people at the club will sit down together and make the right decisions for the future of the club. Those decisions will involve what changes they want to make, technical staff, players, but it's not something to discuss now.
'Everyone knows the type of games we've played over the last few weeks; we've had some big emotions, but there's another game after this one. I've always said that whenever I come back to Stamford Bridge it will be a great feeling.'
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