Alvaro Negredo grabbed a hat-trick and Sergio Aguero struck twice as Manchester City advanced to the Champions League knockout stages with a convincing 5-2 defeat of CSKA Moscow. The result never seemed in doubt after Aguero hit his first from the penalty in the third minute at the Etihad Stadium and the in-form hosts were 3-0 up after an hour. Seydou Doumbia twice disrupted City's flow with a goal on the stroke of half-time and a 71st-minute penalty but Manuel Pellegrini's men were not threatened and secured qualification for the first time with two games to spare.
Robin van Persie missed a penalty and Marouane Fellaini was sent off as Manchester United edged closer to a place in the last 16 with a goalless draw against Real Sociedad. After a poor first half, Javier Hernandez inexplicably failed to tap home Shinji Kagawa's low cross from barely six yards before substitutes Van Persie and Ashley Young took centre stage. Within minutes of their joint arrival, Young provided the cross which Van Persie belted against a post. More contentious was the spot-kick awarded to the visitors when Young went down under Markel Bergara's challenge. Van Persie saw his effort bounce back off the woodwork before clipping goalkeeper Claudio Bravo on the way out and rolling to safety. It was the first time Van Persie had missed from the spot since his failure at Southampton in the first weeks after his arrival from Arsenal. He atoned for that miss by scoring a match-winning hat-trick. There were no such heroics here and with Fellaini red-carded for the first time in his United career for a second yellow card, the visitors were forced to see out the contest with 10 men. However with the other game in the group also ending goalless, no damage was done to United's chances of reaching the last 16, which they will reach with a win from either of their two remaining fixtures.