Cesena was relegated to the Lega Pro Prima Divisione in 2008, when Giaccherini returned and was partnered with Simone Motta in attack.

The club once again reached the top of the table but went on a winless run after the third match as a result of which Luis Jiménez replaced Schelotto as Giaccherini's new attacking partner.

On 8 December 2011, he scored his first goal for the Bianconeri, an angled solo effort in a 2–1 win over Bologna in the Coppa Italia.

Due to injuries and suspensions to first choice centre midfielders Claudio Marchisio and Arturo Vidal, Conte has played him in a more central role.

Juventus won the Serie A title unbeaten that season and reached the final of the Coppa Italia, losing to Napoli.

They also reached the semi-finals of the Coppa Italia and the Quarter-finals of the UEFA Champions League, losing, in both competitions, to the respective winners, Lazio and Bayern Munich.

On 11 July 2013, Juventus manager Antonio Conte confirmed the sale of Giaccherini to English club Sunderland, in order to raise funds.

[7] Sunderland confirmed the signing of Giaccherini on 16 July 2013, on a four-year contract[8] after joining up with his new team during their pre-season training camp near Lake Garda.

[14] Giaccherini appeared as a 77th-minute substitute for Lee Cattermole in the League Cup Final on 2 March, but was unable to prevent Sunderland losing 3–1 to Manchester City.

[16] Giaccherini chose to remain at Sunderland for the 2014–15 season, despite missing out on a place in Italy's squad at the 2014 FIFA World Cup.

[18] After suffering another ankle injury in February in a 3–1 FA Cup win at Fulham, Giaccherini was ruled out for the rest of the season.

Giaccherini played in every match of the tournament and was one of Italy's most important players throughout the competition;[28] in the opening game against Mexico on 16 June, he assisted Mario Balotelli's match-winning goal.

[35] On 13 June 2016, in Italy's first match of Euro 2016, Giaccherini slotted a goal after a half-pitch pass from Leonardo Bonucci to take the lead against Belgium in an eventual 2–0 victory.

[37] In the round of 16 at Stade de France in Paris on 27 June, he assisted Giorgio Chiellini's opening goal in a 2–0 win over defending champions Spain.