 Massaro akaita Italy yake pasi-21 kutanga musi wa 23 Gunyana 1981, mazuva gumi mushure Serie A kutanga kwake Fiorentina. Pakazara, akaita 4 kuoneka ne Azzurrini pakati pa1981 na1984, achitorawo chikamu nechikwata cheItaly cheOlympic pasi pemakore makumi maviri nematatu kumaOlympics a1984, uko Italy yakasvika kuma semi-fainari, ichipedzisa mutambo uyu pachinzvimbo chechina. Zvinoshamisa kuti akavharwa chete 15 nguva yechikwata chevakuru cheItaly, basa raMassaro repasi rose rakapfuura makore gumi pakati pa1982 na1994. Pazera remakore makumi maviri nerimwe, Massaro akaita mutambo wake wekutanga musi wa14 Kubvumbi 1982 pasi paEnzo Bearzot mukukundwa 10 kuEast Germany, uye aive nhengo yechikwata cheItaly chakakunda 1982 FIFA World Cup yakaitirwa kuSpain, kunyangwe asina kuwana nguva yekutamba panguva yemutambo. Akanga asingasviki pakati pa1984 na1986, asi makore masere gare gare akadanwa kuItaly 1994 World Cup squad nemutungamiri Arrigo Sacchi, pazera remakore 33. Akatamba mumitambo mitanhatu yeItaly pamitambo minomwe ye1994 FIFA World Cup yakaitirwa muUnited States, uye akarova zvibodzwa mumutambo wekupedzisira weItaly wechikamu chemapoka musi wa28 Chikumi, uyo wakavabvumidza kuti vafambire mberi kuenda kumakwikwi ekupedzisira sechikwata chechitatu chakanakisa; ichi ndicho chaive chinangwa chake chete kuItaly, uye chakamuita muItaly wepamusoro-soro weItaly paFIFA World Cup, pazera remakore makumi matatu nematatu nemazuva makumi matatu nematanhatu. Mukukundwa neBrazil mufainari yemutambo, akarasikirwa nemukana weimwe-kune-imwe uye akazokundikana kushandura penalty mu shootout. 