Champions League round-up: Feyenoord, Club Brugge and Benfica progress

Julian Carranza’s second-half header dumped seven-times winners AC Milan out of the Champions League as Feyenoord drew 1-1 at San Siro to progress to the last 16 of the competition 2-1 on aggregate.

Milan could hardly have got off to a better start when Santiago Gimenez headed home after Malick Thiaw had flicked on a first-minute corner to level the aggregate scores at 1-1.

Theo Hernandez rattled a post with a 23rd-minute strike, but was then dismissed after being cautioned for diving – his second bookable offence – and his side was made to pay with 17 minutes remaining when Carranza headed the visitors, who had Givairo Read sent off deep into stoppage time, level on the night.

It proved to be a miserable evening for Italian clubs, with Atalanta also going out after Club Brugge wideman Chemsdine Talbi scored twice in a 3-1 victory at the Gewiss Stadium.

Talbi struck after three and 27 minutes to put the Belgian side 4-1 ahead on aggregate, and they were in dreamland when Ferran Jutgla made it 3-0 on the night in first-half stoppage time.

Half-time substitute Ademola Lookman pulled one back within seconds of his introduction but then saw a 61st-minute penalty saved by Simon Mignolet amid a second-half blitz by the hosts, who had defender Rafael Toloi sent off three minutes from time as they slipped to a 3-1 defeat on the night and 5-2 over the two legs.

Orkun Kokcu was Benfica’s hero as they survived a major scare to squeeze past Monaco 4-3on aggregateafter a 3-3 second-leg draw in Lisbon.

Kerem Akturkoglu had given the home side a 22nd-minute lead but goals from Takumi Minamino and Eliesse Ben Seghir turned the game on its head until Vangelis Pavlidis, whose first-leg winner separated the sides before kick-off, converted a