AC Milan took a big step towards joining Rangers in the last 16 of the Europa League after they defeated Rennes 3-0 in the first leg of their play-off match at the San Siro.

The Rossoneri were one of the most high-profile Champions League drop-outs into Europe’s second-tier competition and they will take a sizeable lead to Brittany next week after Ruben Loftus-Cheek scored a double in a straightforward win Stefano Pioli’s men. Fellow Serie A side Roma had a more uncomfortable evening in Rotterdam in the play-offs, drawing 1-1 against Feyenoord – who came out of Celtic’s Champions League group.

Elsewhere, former Hibs winger Abdellah Zoubir scored twice as Qarabag were surprise 4-2 winners away at Braga, while Galatasaray grabbed a stoppage-time winner through Mauro Icardi to defeat Sparta Prague 3-2. Sporting won 3-1 away at Young Boys in Switzerland, while Benfica netted a 98th-minute penalty via Angel di Maria to win 2-1 at home to Toulouse. Two other ties are finely poised after Marseille and Shakhtar drew 2-2, while it was goalless between Lens and Freiburg.

Qarabag's No.10 Abdellah Zoubir - once of Hibs - scored twice as the Azeris overcame Braga 4-2 in Portugal.

Rangers will have watched on with interest given they are safely in the hat for the last 32 already. They won their group last year and as a consequence will be seeded against one of the eight play-off winners when the draw is made on February 23.

Rangers watch Europa League action with interest as AC Milan shine and ex-Hibs forward bags double in shock win