Liverpool and Chelsea both endured forgettable Premier League campaigns but looking to the long-term, the Reds may just have the edge.
Di Matteo somehow salvaged a Champions League trophy from a season that threatened disaster after Chelsea's 3-1 humiliation in Napoli. But victory in Munich merely delayed the inevitable rebuilding process which the Blues have to undertake sooner or later.
Liverpool, in contrast, had no similar success to distract them from the fact that their squad is no longer good enough to compete for a top four place. A League Cup win was a welcome Wembley trip, but Kenny Dalglish's sacking is evidence that the cup was little more than an afterthought in John W Henry's pre-season planning.
Champions League qualification is much more important than the FA Cup, let alone the Carling Cup, and the Reds cannot hide from the fact that their were 17 points off fourth place this season.
But, they are still better placed than Chelsea for long-term success. With the loss of Didier Drogba, Chelsea forward options are a misfiring Fernando Torres, a talented but inconsistent Daniel Sturridge and an untested Romelu Lukaku.
Now, the Blues may spend big this summer on a new marquee striker, and bringing in Gonzalo Higuain, Ramadel Falcao or Edinson Cavani would instantly catapult them clear of Liverpool. But Chelsea's chief executive, Ron Gourlay, has placed his faith in Fernando Torres.
"Fernando Torres is the man that we will go forward with and Fernando Torres will score us the goals," said Gourlay. Such faith is a gamble on past glories and Gourlay is hoping that Torres will eventually come good, but the evidence doesn't inspire much confidence.
The problem for Chelsea is that if they bring in another £40m or £50m striker, Torres will probably leave. He's made it clear he's not happy to play second fiddle, and unless Chelsea change to a two-forward formation, any new striker would expect to start ahead of the Spaniard.
Torres didn't respond well to the competition offered by the 34-year-old Drogba, so to expect him to stick around if Chelsea splash out on another big name is wishful thinking.
Over on Merseyside, the strikers may not have fared much better than Torres, but in Andy Carroll and Luis Suarez, they have a combination which should, in theory, score goals.
Suarez settled well at Anfield, and although Andy Carroll took much longer - almost the whole season - his form picked up drastically towards the end. A solid European Championships and Carroll could be a different player next season.
In midfield, Jordan Henderson patently did not perform to his best last season, but it should be noted he's still only 21 years old. Similarly, Jonjo Shelvy is poised for a breakout campaign next year, the 20-year-old receiving ever increasing minutes in the campaign's final few months.
In defence, Skrtel and Agger formed an excellent partnership - only Manchester United and Manchester City conceded less goals than the Reds last year.
However, a big question mark remains. The search for a Liverpool manager is in danger of dragging on, and Liverpool risk mimicking Wolves tragic search for a boss with every passing week. Frank De Boer and Brendan Rogers have already turned them down, and supporters group Spirit of Shankly has criticised the chaotic style of the recruitment process.
But the Stamford Bridge hierarchy face managerial uncertainty as well, and whoever takes over needs to continue the unpopular rebuilding process started by Andre Villas-Boas. But if Di Matteo stays - a likely scenerio - the old faces will remain, putting off the necessary transition again. In contrast, Liverpool will bring in a new manager, and the favourite is none other than Stamford Bridge's old project manager, Villas-Boas.
That process has already begun in earnest, with Saloman Kalou and Jose Bosingwa reportedly ushered out of the club. Their exits follow Didier Drogba and Chelsea face an difficult transfer window summer looking for replacements.
Liverpool were in this position last season, and after Kenny Dalglish was parachuted in to rescue the Reds from the depths of the Roy Hodgson reign, John W Henry opened his chequebook to invest heavily in a number of new players - most of them under 26.
Not all of those signings worked out, but with a season under their belts expect them to improve next year. A new manager will most likely be able to make a few signings of his own, strengthening their cause further.
An eighth place finish was more than disappointing - it was unacceptable. But as bad as some of the home defeats were last season, there is cause for optimism at Anfield.
The Reds have less debt than Chelsea - potentially an important factor when the Financial Fair Play Rules come into force - and are moving towards a decision on stadium redevelopment with greater purpose than the Blues.
But it's what happens on-the-pitch which counts. The Champions League final felt like the final hurrah for a Blues squad which has stubbornly refused to evolve and they could pay the price next season.
But for Liverpool, it feels like the bottom has been reached. Now the only way is up.