Born in Ancona, Piloni began playing football with the Juventus youth system in 1967, but was later sent to Serie C side Casertana for a season in 1968 in order to gain experience by manager Heriberto Herrera, before returning to Juventus in 1969. He made his Serie A debut in a 2–2 home draw against Varese on 4 April 1971, at the age of 22, under coach Čestmír Vycpálek. That season, he made 7 appearances due to his promising performances, even featuring in the semifinal of the 1971 Inter-Cities Fairs Cup, in a 1–1 away draw against Köln on 14 April. Although it seemed he had overtaken Tancredi, also earning the nickname "Big Pilon", his performances in the first leg of the final against Leeds United, a 2–2 draw, were unconvincing, however, and he was forced to miss the second leg of the final due to injury, which Juventus went on to lose on aggregate. During his time with the Turin club, he was largely a backup to several goalkeepers, including Roberto Anzolin, Roberto Tancredi, and Pietro Carmignani, but was mainly the understudy to legendary goalkeeper Dino Zoff, only making an appearance in the Coppa Italia against Cesena on 6 February 1974 during their time at the club together. In 1975, Piloni moved to Serie B side Pescara, helping the club to obtain Serie A promotion in 1977 for the first time in their history, and making a name for himself as an experienced and reliable goalkeeper. In 1978, following Pescara's relegation, he moved to Rimini for two seasons. He ended his career after a season with Serie D side Fermana in 1981.