Four clubs have secured their place in the UEFA Champions League round of 16 after the conclusion of the first round playoff matches on Tuesday, February 18.

The shocking results came in Italy after AC Milan and Atalanta both crashed out of the competition after losing to Feyenoord and Club Brugge respectively.

The Rossoneri were held to a 1-1 draw at the San Siro as the Eredivisie outfit qualified to the next round 2-1 on aggregate.

Atalanta were also stunned by the Belgium Pro League champions 3-1 at the Gewiss Stadium in Bergamo. Gian Piero Gasperini's side lost 5-2 on aggregate.

In the other remaining matches, Bundesliga giants Bayern Munich and Benfica also booked their place in the last 16.

The Bavarians were held to a 1-1 draw at the Allianz Arena while Benfica played out a thrilling 3-3 draw at Estadio do Sport Lisboa.

Bayern Munich qualified 3-2 on aggregate with Benfica securing their place in the last 16 with an aggregate score of 4-3.

WDN