Trevor Francis was a member of the 1985 Coppa Italia winning Sampdoria side and this week he'll be on Sky Sports to bring you exclusive coverage of the quarter-finals from this year's competition.
Alongside Kate Abdo in the studio, Francis will offer up his expert analysis from four huge fixtures from Italian game and here's what he thinks you should look out for...
ROMA v JUVENTUS - Tue 21 Jan, 7.30pm Sky Sports 3
TREVOR SAYS: Undoubtedly this is the tie of the round and I think most people in Italy would have liked this to have been the final because they're the two strongest teams in Italian football this season.
Juventus have dominated for a while now and won the Scudetto for the past two years and with an eight point advantage over Roma in league at the moment, they look as is they're going to win the championship comfortably again this year.
Roma have had an excellent season under new manager Rudi Garcia with just the one defeat in Serie A and that was against Juventus recently. So this game has all the makings of an excellent tie and I think if it wasn't for the consistent performances of Juve this season, then Roma would probably be top themselves.
Juventus will probably be slight favourites and the reason I say slight is because Roma are playing at home. But Juve don't have a good recent record in the Italian Cup - they haven't won this competition since 1995 - and they've already been knocked out of the Champions League this year which was a big surprise. So I'm going to pick another surprise and say that Roma, with home advantage, will win 2-1.
MILAN v UDINESE - Wed 22 Jan, 7.45pm Sky Sports 3
TREVOR SAYS: Milan have had a very poor season in the league and find themselves languishing in mid-table.
Their former coach Massimiliano Allegri held on to his job longer than anticipated and that was probably down to their continued involvement in the Champions League; he saw them safely through the group stages and some thought he might stay as manager until the end of the season. But, a humiliating 4-3 defeat to Sassuolo in the league meant that Clarence Seedorf has been brought in and he'll see this as a great opportunity to win the competition.
Seedorf will look at what's left in the draw and see that one of the best two teams in Roma or Juventus will be gone and despite the fact that Milan are below Udinese in the league, they will start as slight favourites.
I'm going to predict that an inspirational performance from Mario Balotelli will help Milan to a 2-1 home victory.
FIORENTINA v SIENA - Thu 23 Jan, 7.45pm Sky Sports 3
TREVOR SAYS: Fiorentina are one of the stronger teams in Italian football. I've mentioned Roma and Juventus who are top, then Napoli in third but la Viola are fourth behind them and they have, in coach Vincenzo Montell, someone we know from his brief spell he has a player on loan at Fulham in 2007, who is now doing a great job.
I think that Fiorentina have the easiest game and I say that with the greatest respect to Siena, who were in the top division last year but were relegated and are now finding adapting to life in Serie B difficult, so they've done well to get to the quarter-finals.
But I think that Fiorentina - the team that inflicted the only defeat on Juventus this season in the league - can be very strong at home and should overcome Siena. I predict a 3-0 victory for the home team.
NAPOLI v LAZIO - Wed 29 Jan, 7.30pm channel tbc
TREVOR SAYS: Napoli are in third in Serie A but were of course, terribly disappointed to be knocked out of the Champions League, finishing just behind Arsenal and Borussia Dortmund; but they acquitted themselves pretty well in that competition.
In cup competition the Neapolitans are very useful and they haven't let that European disappointment affect their league form, because they're still playing well. I also think that in Gonzalo Higuain and Jose Callejon they've got two very good players who they've taken from Real Madrid.
This game is going to be close because Lazio are the current holders and beat their arch-rivals Roma in last year's final, so this is a very interesting game and I think due to the fact that Napoli are playing at the Stadio San Paolo - which is always difficult to play at because of the fantastic and passionate home support - they'll edge this one 2-1.