KHARKIV, Ukraine: Shakhtar Donetsk advanced to the knockout stage of the Champions League with a 2-1 victory over Manchester City on Wednesday, ending the English club's unbeaten record in all competitions this season.
In freezing temperatures against a Shakhtar team which only needed a draw to be sure of qualifying, City struggled to cope with rapid counter-attacks by the Ukrainian side's Brazilian forwards.
Defeat means City, which had already qualified as Group F winner, failed to become only the seventh club in Champions League history to win every game in the group stage.
Wednesday's results
GROUP E
Liverpool 7-0 Spartak Moskva
NK Maribor 1-1 Sevilla
GROUP F
Feyenoord 2-1 Napoli
Shakhtar Donetsk 2-1 Manchester City
GROUP G
FC Porto 5-2 Monaco
RB Leipzig 1-2 Besiktas
GROUP H
Real Madrid 3-2 Borussia Dortmund
Tottenham Hotspur 3-0 APOEL
Tuesday's results
GROUP A
Benfica 0-2 Basel
Manchester United 2-1 CSKA Moskva
GROUP B
Celtic 0-1 Anderlecht
Bayern Munich 3-1 PSG
GROUP C
Chelsea 1-1 Atletico Madrid
Roma 1-0 Qarabag
GROUP D
Barcelona 2-0 Sporting CP
Olympiakos Piraeus 0-2 Juventus
With one eye on Sunday's Manchester derby, City coach Pep Guardiola gave starts to youngsters Phil Foden on the left and Tosin Adarabioyo in the centre of defence.
Shakhtar started aggressively and took the lead in the 26th minute when Bernard cut in from the left side of the box and curled a shot inside the far post, beyond the reach of goalkeeper Ederson.
Eight minutes later, Ederson was left helpless in a different way for Shakhtar's second goal as Marlos passed into space behind the City defence. Ismaily, already in behind right-back Danilo, sprinted to beat Ederson to the ball before rounding the keeper and stroking a shot into the unguarded net.
City earned a consolation goal in added time when Sergio Aguero scored from the penalty spot after Bogdan Butko brought down Gabriel Jesus.
It was City's first competitive loss since being beaten by Arsenal in an FA Cup semifinal in April. City had been unbeaten in 28 games since then, 22 of them this season.
Feyenoord beat third-place Napoli 2-1 in Wednesday's other game in Group F.
At Liverpool, Brazilian Philippe Coutinho struck a hat-trick as Liverpool crushed Spartak Moscow 7-0 to move into the knockout stages as Group E winners.
Spartak finish third in the group, behind second-placed Sevilla, and move into the Europa League.
Liverpool manager Juergen Klopp fielded an attacking lineup with Sadio Mane, Roberto Firmino and Mohamed Salah in attack, with Coutinho playing behind them, and it was simply too much for the Russians to handle.
The five-times European champions took the lead in the fourth minute with a Coutinho penalty after Salah was pulled down by Georgi Dzhikiya.
Spartak allowed Liverpool’s attacking trident far too much space and they took full advantage in the 15th minute with a super team goal as Mane fed Salah, who slipped the ball inside to Firmino to set up his compatriot, Coutinho, for a simple finish.
Three minutes later, Liverpool added their third. Mane chipped the ball into the box, Spartak defender Serdar Tasci failed to clear and Firmino accepted the gift and confidently drove home.
But having given up a 3-0 halftime lead in their last Champions League outing in Sevilla, Liverpool were in no mood to drop down a gear and they put the game to bed within five minutes of the restart.
James Milner whipped in a cross from the left which Mane met first-time with an unstoppable volley and then a deflected shot from Coutinho completed his hat-trick to make it 5-0.
Mane got his second when he scooped in a low cross from Georginio Wijanaldum in the 76th minute, and then Salah, who had been outstanding all evening, made it 7-0, blasting home after some typically clever footwork in the box.
It is Liverpool's second 7-0 win in the group following their victory by the same scoreline against Maribor in Slovenia in October.
In Madrid, Real Madrid's Cristiano Ronaldo set a record for scoring in every Champions League group game as his side won an entertaining encounter 3-2 over Borussia Dortmund, who clinched a spot in the Europa League.
Fernando Llorente scored his first goal for Spurs as they rounded off their impressive group stage campaign by strolling to a 3-0 home win over APOEL Nicosia.
Tottenham, who were already guaranteed to finish top of Group H ahead of Real Madrid and Borussia Dortmund, ended with 16 points and five wins from six games. APOEL finished bottom with two points.
Llorente, who joined Spurs from Swansea City in the summer, opened his account for the club in the 20th minute when he beautifully controlled a low cross from Serge Aurier and swivelled before firing into the net.
Tottenham, who made eight changes to the team that started against Watford on Saturday, doubled their lead after 37 minutes when Son Heung-min curled the ball into the far corner and Georges-Kevin N'Koudou made it 3-0 with 10 minutes remaining.
Real were guaranteed a place in the last 16 as Group H runners-up behind Tottenham Hotspur, but coach Zinedine Zidane still fielded a strong side for the game, only resting Marcelo, Karim Benzema, Toni Kroos and Luka Modric.
Real's Spanish striker Borja Mayoral got his first Champions League goal in the eighth minute with a chipped finish from close range while four minutes later Ronaldo struck for the sixth group game in a row, sending a wonderful curled shot into the top corner from outside the box.
Dortmund striker Pierre-Emerick Aubameyang led a short-lived fightback by scoring either side of the break for the Germans, who have failed to win a game in the group stage campaign, but finished above APOEL Nicosia on goal difference to qualify for the Europa League.
Real averted a third consecutive draw in all competitions thanks to an 81st-minute strike from Lucas Vazquez to end their group campaign with 13 points.
They could, however, be without defender Raphael Varane for the next few games after the Frenchman limped off with a muscle injury.
Vincent Aboubakar struck two first-half goals to spearhead Porto's emphatic 5-2 win over Monaco at the Dragao Stadium to seal their place in the knockout stages.
The prolific Cameroonian striker took his season's tally in all competitions to 17 in a one-sided game in which both teams were reduced to 10 men after Porto's Felipe and Monaco's Rachid Ghezzal were sent off for an undignified 38th-minute scuffle.
Knowing a win would guarantee them second place in Group G, Porto's nerves were quickly settled when Aboubakar latched on to Yacine Brahimi's through ball after nine minutes.
The powerful striker was in magnificent form, pouncing again in the 33rd minute when he cut in from the left edge of the box and shot beneath Diego Benaglio for his fifth goal of the Champions League campaign.