Pedzisa mutsara unotevera: Musi wa 19 Chikumi 2012, Di Francesco akagadzwa semurairidzi mukuru weSerie B divi Sassuolo. Pakupera kwegore ra2012-13, akatungamira Sassuolo kuenda kuSerie B championship uye kukwidziridzwa kumushandirapamwe wepamusoro. Akadzingwa basa musi wa 28 Ndira 2014 mushure mekushaiwa mhedzisiro, achizogadzwazve pachinzvimbo musi wa 3 Kurume 2014 mushure mekunge mhedzisiro isina kuvandudzika mukusavapo kwake. Kubva munaKurume 2014 zvichienda mberi, mhedzisiro yakavandudzwa uye Di Francesco akabudirira kudzidzisa kuchengetedza Sassuolo kubva pakuburitswa pasi nekuda kwekuteedzana kwemhedzisiro yakanaka (13 mapoinzi mumitambo minomwe yekupedzisira yemwaka). Muna June 2014, zvakaziviswa Di Francesco akanga asaina kuwedzera kuti acharamba naye chibvumirano pamwe Sassuolo kusvikira June 2016. Akawedzera zvakare kondirakiti yake muna Kubvumbi 2016, iyo yaizogara kusvika Chikumi 2019. Sassuolo akapedza
2015-16 Serie A mwaka ari pachinhanho chechitanhatu, achiisa chisimbiso munzvimbo yechitatu yekukodzera ye2016-17 UEFA Europa League. Mwaka wakatevera, Sassuolo yakakwanisa kuenda kuEuropa League play-offs pasi paDi Francesco, uye pakupedzisira yakavhara nzvimbo muEuropa League group stage.