Sporting moved ever closer to winning a first Portuguese league title in 19 years after comfortably winning 2-0 away to Rio Ave on Wednesday.
Seven-times European champions AC Milan scored a penalty at the end of extra-time before winning a 24-penalty shootout against Portugal's Rio Ave.
Sporting Lisbon defender Sebastian Coates endured a nightmare evening as he conceded three penalties and was sent off in the same game.
Fabio Coentrao said the reason he agreed to cancel his contract at Real Madrid with a year left was because he wanted to be happy.
AaB progressed into the Europa League last-32 despite Yonathan Del Valle's second-half brace handing Rio Ave a 2-0 victory in their final Europa League Group J clash at the Estadio do Rio Ave.
Tottenham came from behind to take a 2-1 win in the first leg of their Europa League qualifying play-off against AEL Limassol.