Ajax 0 AC Milan 0Ajax Amsterdam and AC Milan battled to a goalless stalemate in Amsterdam to leave the Italians favourites to reach the last four of the competition.
Despite some high-quality passing and goal chances for both teams, neither side could find the net, but Milan will be the happier with the home leg to come on April 23rd.
The winners of this tie will play either Inter Milan or Valencia in the semi-finals early next month.
The Dutch side's coach, Ronald Koeman, was hellbent on sending packing a Milan outfit which swamped his old Barcelona side in the 1994 final. The following year, Ajax captured the trophy themselves, but since then both clubs have struggled.
Milan coach Carlo Ancelotti adopted a cautious approach from the start, leaving Rivaldo and Jon Dahl Tomasson on the bench, although Filippo Inzaghi shrugged off a lingering bout of flu to take his place in attack.
The visitors, who pushed Real into runners-up spot in the second group phase, still made plenty of early running with Andriy Shevchenko looking lively along with Rui Costa.
Also in the midfield for the Italians was Clarence Seedorf, who before a spell with Real had lifted the Cup with Ajax and at Milan's expense in 1995.
Ajax were comparatively light on such experience, with Finnish midfielder Jari Litmanen starting on the bench following three months out with Achilles trouble while striker Andy van der Meyde was suspended.
Shevchenko forced a fine save from Ajax's Romanian goalkeeper Bogdan Lobont after Inzaghi played him in on the right side of the box after just five minutes.
Seedorf then set his sights on the quarter hour mark only for Cristian Chivu to recover some ground and block.
Czech international midfielder Tomas Galasek responded with a long-range effort which flew well over Dida's bar.
Milan midfielder Gennaro Gattuso picked up a booking 10 minutes before the break for a foul on John O'Brien and will now miss the second leg in a fortnight.
Both sides upped the tempo after the break but still both defences held firm, prompting a rash of attacking substitutions in the closing 15 minutes.
Milan sent on Tomasson for Inzaghi and Rivaldo for Shevchenko in quick succession while Litmanen finally made his entrance for Zlatan Ibrahimovic.
Still, true chances proved few and far between as Welsey Sneijder, on for Galasek, scooped an effort wide for Ajax on 79 minutes.
At the other end Massimo Ambrosini drew a fine save from Lobont on a rare Milan breakaway.
Yet the Dutch were unable to break down the Italians' defensive barriers, with Paolo Maldini and Alessandro Nesta outstanding in the Milan back line, as they made it eight draws in 13 Champions League matches.
AJAX: Lobont, Trabelsi, Chivu, Pasanen (De Jong 73), O'Brien, Galasek (Sneijder 67), Pienaar, Maxwell, Yakubu, Van der Vaart, Ibrahimovic (Litmanen 73). Subs Not Used: Didulica, Bergdolmo, Witschge, Boukhari.
AC MILAN: Dida, Maldini, Nesta, Simic, Costacurta, Gattuso, Rui Costa, Seedorf (Serginho 26), Ambrosini, Shevchenko (Rivaldo 79), Inzaghi (Tomasson 73). Subs Not Used: Abbiati, Helveg, Laursen, Brocchi. Booked: Gattuso, Ambrosini.
Referee: Terje Hauge (Norway)
