Celtic came agonisingly close to booking a place in the quarter-finals of the Champions League only for their European dream to come to an end in frustration. They withstood an AC Milan onslaught to take the game at the San Siro to extra time but a stunning goal from Kaka early in the additional period proved the difference between the sides. The Brazilian midfielder had earlier been denied by the crossbar but showed pure class to put the six-times European champions into the last eight. The Italians created numerous opportunities throughout the game but the goal proved elusive in normal time, just as it had in the opening leg at Parkhead. Celtic did show plenty of fighting spirit but failed to find the finishing touch against the experienced Rossoneri.
The game began at a frenetic pace, with both teams determined to impose their play. Roared on by an enormous bank of supporters, Celtic showed confidence early on but it was Milan who had the first chance of the game. Celtic goalkeeper Artur Boruc was forced to stretch fully to palm away Kaka's left-footed strike towards the far post. Celtic replied with Shunsuke Nakamura's free-kick finding Jiri Jarosik at the far post but his effort was blocked by Paolo Maldini for a corner. The Bhoys continued to press forward but struggled to get past Milan's defensive wall and soon found themselves having to do their own share of defending. Stephen McManus, who had recovered from a groin injury, twice read Marek Jankulovski's intentions inside the box with the midfielder ready to fire on target. Nakamura wasted a good chance with his 30-yard free-kick proving an easy catch for goalkeeper Nelson Dida. Midway through the first half, Lee Naylor cut out a pass from Clarence Seedorf at the far post as Inzaghi looked ready to strike home. Celtic missed another good chance to test Dida as Aiden McGeady failed to control Jan Vennegoor of Hesselink's clever pass on the edge of Milan's area. On the half-hour mark, Darren O'Dea did well to cut out Kaka's pass towards Inzaghi and the defender remained heavily involved as Nakamura struggled to keep up with Seedorf's runs on the left. O'Dea cleared Kaka's bullet strike from Seedorf's cross as the Celts had another lucky escape. Despite Milan's chances, Celtic could have gone in at half-time with a 1-0 lead but Jarosik's diagonal left-footed strike went wide of Dida's far post.
Milan picked up where they left off after the restart and Seedorf's long-distance effort failed to find the target while Andrea Pirlo's central free-kick provided an easy catch for Boruc. On 50 minutes, Inzaghi got behind Jankulovski's cross but his angled volley went wide. On the hour-mark, Maldini anticipated McGeady's run into the box as he tried to get behind Vennegoor of Hesselink's clever assist. Gordon Strachan made his first substitution soon after with Thomas Gravesen replacing Jarosik. Gravesen almost made an immediate impact but his powerful strike inside the area was blocked by Maldini. On 71 minutes, McManus was forced to make a vital clearance from Inzaghi's header while seconds later Massimo Ambrosini's header fizzed wide of the far post. In the 84th minute, Boruc made a decisive save from Maldini's close-range header. While at the other end, Celtic fans demanded a penalty after Ambrosini had pushed Nakamura inside the area but the referee played on. Boruc kept Celtic's Champions League hopes alive with a stunning save from Seedorf's strike before Kaka struck the crossbar in what was the last opportunity in normal time.
Celtic finally conceded early in extra time and the goal proved a hammer blow and they almost gave away a second shortly after with Pirlo's close-range effort forcing Boruc to dive to his left to clear. The Hoops never lost hope but mustered little with the exception of a Gravesen's effort. Boruc kept his team's hopes alive with a one-handed save from Pirlo's right-footed shot. At the other end, Craig Beattie's header from Neil Lennon's cross went high over the crossbar as time ran out for Celtic.
AC Milan: Dida, Oddo (125 Simic ), Bonera, Maldini, Jankulovski, Gattuso (79 Brocchi), Pirlo, Ambrosini, Seedorf, Kaka, Inzaghi (73 Gilardino)
Subs not used: Kalac, Favalli, Gourcuff, Oliveira
Celtic: Boruc, Telfer, McManus, O'Dea, Naylor, Nakamura (105 Miller), Lennon, Sno (97 Beattie), McGeady, Jarosik (62 Gravesen), Vennegoor of Hesselink
Subs not used: Brown, Wilson, Kennedy, Riordan,
Ref: Konrad Plautz