Piccareta followed Di Canio to Premier League Sunderland in March with the job of avoiding relegation. They just about achieved survival but a dismal start to the following season saw Di Canio and Piccareta leave in September 2023. That would mark the end of what Picarreta describes as the most 'important' stage in his career.
After England, Piccareta's career took him far and wide in senior and youth football before he joined up with Di Biaggio at Albanian side Dinamo City, another experience from the Italian that had highs and lows.
In a fascinating interview with TribalFootball, Piccareta reveals what it was like working with Di Canio and Di Biaggio and much more.
You were the assistant manager to no other than the famous Paolo Di Canio at Swindon and then Premier League Sunderland for a short period. Can you tell me a bit about what it was like working with Di Canio?
"Working with him was a unique experience for me, and if you think I was the only one to work with him during his time as a coach. Because in his two only experiences as a coach, I was his assistant at Swindon and Sunderland.
"I worked with him for four years and they were beautiful years for us that taught us a lot. During those years we achieved success as we failed.
"I will always be grateful to him because he chose me as his assistant coach. Working with him was difficult because in the public eye and in the media, he seemed a very hard character to get along with but in private he is a very humble guy, he treats you always with great respect and helps you a lot.
"We got along very well with each other, and we created a great relationship on and off the pitch.
"Also, I learned a lot from him because for me he was a really good coach and he has always achieved success. In the end, I can say that for me it's a bad thing that he didn't continue to coach because I am sure he had a lot of things to give to the football world."
And how would you compare that experience to your more recent position as the assistant coach at Dinamo City in Albania working alongside another Italian legend Luigi Di Biaggio?
"Di Biaggio from a character point of view is different to Di Canio, Luigi wants always to win and has his philosophy of playing who try always to implement to his teams but is calmer then Di Canio and so working with him is a little bit more easily.
"In Albania we tried to implement a methodology different from what the players used and what Di Biaggio has used in his experiences in Italy, especially in the national team. Probably we didn't understand the dynamics of Albanian football or the players that we had at our disposal and maybe we weren't good with each other as staff because we knew each other at the last moment.
"Also, I want to add that at some moment during the games we were unlucky, and despite that we were performing well.
"But the results weren't coming, and so players lost their belief. So, in the end we gave our resignation. But for me the level of Albanian football is high, and this is demonstrated by the fact that different Albanian players go and play abroad and have a lot of success."
You worked for Roma's u17s in the past, what have you made of fellow Italian Daniele De Rossi's time as the manager so far since taking over from Jose Mourinho?
"I think that Daniele (deserves) huge merits for the change in performances and results that Roma has had in the last few weeks.
"Mourinho at Roma was like a king and the fans adored him and were thankful to him for the achievements that he brought to the club, but I think he made a mistake because he didn't understand the fans that wanted a more attacking style of football for their team. And for me, he could try a little bit more this thing and could risk a little bit more.
"Daniele for me understood the situation very well and changed things and put the players differently on the pitch with a more attacking style of play than before.
"And now you can see the players which enter the pitch and play with more pleasure and are freer in their mind and try more things than before."
And what are your thoughts on the current Serie A season as a whole?
"In my opinion in the last few years the Italian league is getting back to the levels of the past. Inter are doing something unbelievable, such great performances which are leaving the other teams in the shadow.
"The surprise of this season is, of course, Bologna. Motta is doing a great job there and he (allows) his young players to express themselves as best as they can. And for me, the disappointment of this year is Napoli, despite the fact they might not repeat last season, I never thought they would have so many problems."
What are your expectations for Italy at the Euros this summer?
"Italy is not at the same level as some other national teams like France, England, Germany, and Spain. Luciano is a great coach and has brought a lot of enthusiasm to our national team and he is trying to implement his style of play to our national team.
"On an individual level the other teams are better than us and that's why our coach is trying and should be focused on the collective level, to fully implement his attractive style of play on our team.
"The favourites to win this tournament for me are France and Spain."
Finally, what are your hopes for your future in coaching? Any dream jobs?
"My future is unpredictable because my journey until now has been {unpredictable). I hope that my future is in England because that is my dream to be the head coach of any English team in the Premier League."
- adapted by Harry Dunnett