Champions League Round of 16 draw 1st leg: Feb 14 / 15, 21 / 22 Head-to-head 2nd leg: Mar 7 / 8, 14 / 15 Manchester City ENG Semi-final Semi-final 2016 First meeting Last season Best finish AS Monaco FRA Did not play Final 2004 Real Madrid ESP Winner 11-time winner W1-D1-L0 Napoli ITA Did not play Last 16, 2012 Benfica POR Quarter-final Winner 1961, 1962 W1-D0-L1 Dortmund GER Did not play Winner 1997 Bayern Munich GER Semi-final 5-time winner W5-D2-L3 Arsenal ENG Last 16 Final 2006 Porto POR Group stage Winner 1987, 2004 W0-D1-L2 Juventus ITA Last 16 Winner 1985, 1996 Bayer Leverkusen GER Group stage Final 2002 W1-D2-L1 Atletico Madrid ESP Final Final 1974, 2014, 2016 Paris St-Germain FRA Quarter-final Semi-final 1995 W2-D3-L4 Barcelona ESP Quarter-final 5-time winner Sevilla ESP Group stage Quarter-final 1958 Leicester City ENG Did not play Debut QUARTER-FINALS Apr 11 / 12, 18 / 19 SEMI-FINALS May 2 / 3, 9 / 10 CHAMPIONS LEAGUE FINAL Jun 3, National Stadium, Cardiff Source: UEFA, GracenoteFirst meeting