In the early hours of this morning, the Coppa Italia round of 16 was released, and the Milan duo were divided into the same half.

The Milan duo were divided into the bottom half of the Coppa Italia round of 16, with the two teams facing Genoa and Empoli respectively, and if all goes well, they may meet in the semi-finals.
Coppa Italia round of 16 against the top half:
Juventus vs Sampdoria
Cagliari vs Sassuolo
Naples vs Florence
Atlanta vs Venice
Coppa Italia round of 16 against the bottom half:
AC Milan vs Genoa
Lazio vs Udinese
Roma vs Lecce
Inter Milan vs Empoli