Eliaquim Mangala (left) of Manchester City fights for possession against Marlos of Shakhtar Donetsk in Ukraine on Wednesday night. Photo: Sergey Dolzhenko/EPA

Shakhtar Donetsk booked a Champions League knockout-stage berth after first-half goals by Brazilians Bernard and Ismaily gave the Ukrainian side a 2-1 win over Manchester City in Group F on Wednesday.

City, who suffered their first defeat of the season in any competition, finished top with 15 points, three more than Shakhtar and nine ahead of third-placed Napoli, who dropped into the Europa League after a 2-1 defeat at bottom team Feyenoord.

With one eye on Sunday’s Premier League Manchester derby against United, City coach Pep Guardiola rested his entire first-choice back four, and Shakhtar took advantage as they romped into a 2-0 lead before halftime.

Needing only a draw to be sure of qualifying, the home side launched waves of attacks instead of sitting back as Bernard curled a superb shot from 15 metres past City keeper and compatriot Ederson in the 26th minute.

Ismaily added the second six minutes later, capitalising on Ederson’s error and beating him to a long ball by Marlos before stroking it into an empty net to delight a full house in Kharkiv.

Taison twice fired narrowly over the bar either side of the break as Shakhtar kept up the pressure before late substitute Sergio Aguero netted a stoppage-time penalty for City.

Aguero blasted his spot-kick past keeper Andriy Pyatov, but it was scant consolation for City coach Guardiola, who had little to cheer on his 100th Champions League appearance as manager.

The draw for the last-16 is in Nyon, Switzerland, on Monday and Premier League leaders City will head a pack of five English teams in the knockout stages, with Liverpool, Manchester United, Chelsea and Tottenham Hotspur also through.

Champions League Results

Shakhtar Donetsk 2-1 Manchester City

Liverpool 7-0 Spartak Moscow

Tottenham Hotspur 3-0 APOEL Nicosia

Real Madrid 3-2 Borussia Dortmund

RB Leipzig 1-2 Besiktas

Maribor 1-1 Sevilla

FC Porto 5-2 Monaco

Feyenoord Rotterdam 2-1 Napoli

Group Winners

Manchester United, Paris St Germain, AS Roma, Barcelona, Liverpool, Manchester City, Besiktas, Tottenham Hotspur


Basel, Bayern Munich, Chelsea, Juventus, Sevilla, Shakhtar Donetsk, FC Porto, Real Madrid