
After previously reviewing the market for goalkeepers, defenders and midfielders, it’s now time to take a look at the winger market in Serie A. Let’s first take stock of the current options available to the top Italian teams going into the summer window:
Juventus- Douglas Costa got off a fast start before becoming an after thought following some injuries and an off field issue (on top of the spitting incident), Bernardeschi showed pretty good chemistry with Ronaldo although his stats were underwhelming, Mandzukic continues to often play on the wing. Cuadrado struggled with a severe injury in second half of the season, while Cancelo’s defensive limitations could see him playing in a more advanced position next season.
Napoli- Callejon is now 32, Insigne started the season playing as a second striker, Younes showed flashes the few times he played and Ounas made the most of the opportunities given to him by Ancelotti- which were more frequent than under Sarri but still probably not enough for a 22 year old looking to break out. Simone Verdi continued to battle with injuries and is probably at best a super sub moving forward.
Inter- while Perisic did perform better in the final stretch of the season, he continued to disappear for months at a time. Politano was a very pleasant surprise and the best new addition along with De Vrij- he will certainly be redeemed from Sassuolo after his first season on loan with option to buy. Candreva continues to be hit like a pinata by Inter fans on Twitter
Atalanta- we covered Hateboer, Gosens and Castagne in the wing back article since they cover that role in Gasperini’s formation.
Milan- Suso and Perisic had similar seasons but at least peaked when it matters most. Castillejo wasn’t nearly as impactful as Deulofeu and could return to Spain, Bonaventura continues to rehab from his surgery while Calhanoglu hasn’t yet shown he can be a quality/consistent starter moving forward.
Roma- as great as El Shaarawy was this season, it’s not a good sign that he was clearly the club’s best winger (and probably best player period) over highly rated prospects like Cengiz Under and Justin Kluivert.
Lazio- we covered most of their players at this position in the wingback section since Simone Inzaghi runs a similar system to Gasperini’s but Angel Correa could play as a winger with a new manager and was the club’s best player in second half of the season.

Federico Chiesa- Fiorentina’s disastrous season makes him much more likely to leave, but has his value taken a hit since he’s the signature player on the most underachieving Serie A team of the season? Napoli had previously offered close to 50 million to acquire him and could still use him, while Chiesa has also been linked to Juventus and Inter. Chiesa is obviously very talented and only 21 years old, but this season he was more known for diving than scoring goals or delivering assists.
Douglas Costa- there are few players more electrifying in Serie A than the Brazilian international, but between the spitting incident in the match against Sassuolo and deciding to go to Neymar’s birthday party right after being involved in a car accident, it remains to be seen if Juventus, a club known for not tolerating these sorts of things, decide to hold on to him. But considering that they invested significantly to acquire him on a permanent basis from Bayern Munich (another club who got fed up with his off field antics) just last summer, he’s not a player they can turn a plusvalenza on easily despite his considerable skills.
Keita Balde’- while Inter will certainly redeem the rights to Politano, it’s unlikely they’ll pay Monaco over 30 million to keep the former Lazio winger permanently- but considering their excellent relationship with his new agent, they could look to extend the loan. Keita struggled at first because he didn’t get much of a summer retreat and later battled injuries so another team could try to capitalize his considerable talent.
Ivan Perisic- Inter may regret not selling him after his excellent World Cup but at least his late season contributions could help them clinch a Champions League spot (I’m writing this a few days before final match of the season). Perisic has been linked to Premier League teams for the past two years and as recently as January when he came close to joining Arsenal and with Conte arriving, it’s likely that the nerazzurri will go for a more natural fit in 3 5 2.

Cengiz Under- following Roma’s deep run in the Champions League last season, the Turkish winger was being mentioned as a player worth 50 million but the giallorossi decided to keep him after cashing in on Alisson, Strootman and De Rossi so he could be part of their young core. While Under didn’t have nearly as a good a season, Arsenal and Spurs continue to be mentioned as possible destination for him.
Suso- the former Liverpool winger has a 40 million exit clause and Milan have been trying to negotiate a new deal to increase it or eliminate it altogether, but so far Suso is requesting to be paid as much as Donnarumma and it’s hard to imagine the rossoneri wanting to pay him nearly that much.
Hakan Calhanoglu- the Turkish international best chance at staying is for Gattuso to be confirmed as Milan manager, if not it’s likely he’ll either head back to the Bundesliga or the Premier League where he has been linked to Leicester City.

Lorenzo Insigne- after a stellar start to the season, Napoli’s home town star struggled considerably and looked more like the player we are (unfortunately) accustomed to seeing on the Italian national team. Insigne recently formalized his relationship with Mino Raiola as his agent, but while a transfer can’t be completely excluded, it’s more likely he’ll sign a new contract with Napoli and become arguably the biggest “bandiera” left in Serie A after Chiellini.
Rodrigo De Paul- after three seasons at Udinese, the former Racing winger/attacker is ready to take the next step in his career especially considering he also made his debut on Argentina’s national team. Napoli and Inter have been heavily linked to him and both clubs have an excellent relationship with Udinese.
Riccardo Orsolini- few players were more impactful in the second half of the season than the Bologna winger whom Juventus still own. The 22 year old could be used as part of a package by the bianconeri to acquire a bigger name (perhaps Chiesa or Milinkovic Savic) and should absolutely be considered an intriguing player for the Azzurri’s senior squad.

Papu Gomez/Josip Ilicic- Atalanta’s current captain must be thrilled he never left to go play in the Middle East considering his club’s stellar season. Could he look for a huge pay day at the age of 31? It’s hard to envision that should Gasperini stay and if they qualify for the Champions League. Ilicic on the other hand has just one year left on his contract and has already agreed to personal terms with Napoli, it will be up to Atalanta to decide if they want to give him a raise after a stellar season.