Nicky Butt 's United under 19s lost their first UEFA Youth League match of the campaign in Moscow, where they were comprehensively beaten 4-0 by CSKA.
The young Reds struggled to get going in the October Stadium and were a goal down after 13 minutes when Axel Tuanzebe handled. CSKA striker Timur Zhamaletdinov put away the penalty.
Despite the sun in the Russian capital the temperature was at zero but United's kids preferred not to wear gloves, like their hosts, and they showed their mettle in a brave effort to fight back.
However without injured prolific striker Marcus Rashford, the Reds struggled to pose a threat in the box. Seconds before half-time Makarov added a second.
Before United could think about a serious comeback CSKA scored again with a second penalty after the interval. Zhamaletdinov was lethal again from 12 yards after Tyrell Warren had handled.
The teenage Reds' spirit had now disintegrated and the Russians were all over them and creating chances. They were opened up in the 88th minute when Gordyushenko broke through and slipped home the fourth.
United: Henderson, Reid,Tuanzebe, Fosu-Mensah, Dearnley(Diedrick-Roberts 64) Gribbin, Redmond, McTominay, Hamilton, Warren, Kehinde (Whelan 62)