A Roma youth product, he was signed on loan by then-Serie D club Palermo on 30 December 2019, effective from the January 2020 transfer window.[3]
Silipo consistently played in the second half of the 2019–20 Serie D season that was cut short due to the COVID-19 pandemic in Italy, with his performances leading Palermo to sign him permanently following the club's promotion to Serie C; he signed a four-year deal, with an option for Roma to buy him back within two years.[4]
On 26 August 2022, after two Serie C campaigns which saw him primarily used as a backup, Silipo was loaned out to Serie C club Juve Stabia.[5]
On 11 August 2023, Palermo announced the sale of Silipo to Serie C club Monterosi on a permanent transfer.[6]
After a season with Monterosi that eventually ended with relegation, Silipo was signed by newly-relegated Serie C club Ascoli on 6 August 2024.[7]