Celtic FC and AC Milan played out a goalless draw in the first leg of their UEFA Champions League first knockout round tie in Glasgow.
The best opportunity fell to Alberto Gilardino midway through the first half but he was denied by a superb reflex save from Celtic goalkeeper Artur Boruc, while moments earlier Jan Vennegoor of Hesselink failed to convert an opening from a Shunsuke Nakamura free-kick.
Carlo Ancelotti had identified Nakamura as one of the main threats and the Japan midfielder demonstrated why on nine minutes, whipping in a dangerous free-kick from the Celtic right. The ball arrived at the feet of Vennegoor of Hesselink, who had shaken off a hamstring strain to lead the home attack, but he seemed to be taken by surprise, allowing goalkeeper Zeljko Kalac to gather the loose ball. The Dutch international was causing some anxious moments for Paolo Maldini and the Milan captain, celebrating his 100th UEFA Champions League appearance, was booked for a late lunge at the centre-forward.
Play was swinging from box to box with both sides committed to attack. Kenny Miller tested Kalac with a low effort after being played in by Aiden McGeady, while Yoann Gourcuff - in for the injured Clarence Seedorf - got on the end of a cross from Andrea Pirlo but headed meekly at Boruc. The visitors should have opened the scoring just before the half-hour, however, when Kaká sent Gilardino through. The striker had time to set his sights and curl a right-foot shot towards the far corner only to be denied by Boruc's outstretched foot, the Poland No1 turning the ball past the post and to safety.
Milan were now enjoying the bulk of possession in midfield, and Massimo Ambrosini and Gilardino passed up decent half-chances from the edge of the area. With half-time approaching Nakamura troubled Kalac again with a long-range set-piece but the Australian international was equal to the task, smothering the shot low to his left.
Celtic showed more composure after the break and, within minutes of the restart, McGeady brought another stop from Kalac with a snapshot from 20 metres. However, Milan were still fashioning the better openings and Gennaro Gattuso should have done better on 52 minutes when Pirlo freed him with another defence-splitting pass. The former Rangers FC favourite slid his attempt the wrong side of Boruc's left-hand post. At the other end, left-back Lee Naylor went close with a rasping drive which rose just over the junction of post and crossbar.
Gordon Strachan sacrificed Miller for Jiří Jarošík with half an hour to go, but it made little difference to the pattern of play with Milan pouring forward looking for a priceless away goal. In the closing minutes Celtic pressed for the breakthrough that would give them a slender advantage for the return game but Vennegoor of Hesselink could not connect with another tempting Nakamura cross, making Milan the favourites to progress to the quarter-finals.