Tottenham will have to produce a Champions League comeback after Brahim Diaz gave AC Milan a narrow win in the first leg of their last-16 tie at the San Siro.
Diaz nodded in early on after Spurs goalkeeper Fraser Forster had saved a Theo Hernandez shot and then superbly got a hand on the scorer's initial follow-up attempt.
Antonio Conte's side looked relatively comfortable for long periods of the contest against the seven-time European champions - as a youthful pairing of Pape Sarr and Oliver Skipp deputised ably for the suspended Pierre-Emile Hojbjerg and the injured Rodrigo Bentancur in midfield.
However, they were rarely able to build any attacking momentum with their front three of Harry Kane, Son Heung-min and, until his withdrawal, Dejan Kulusevski well shackled by a disciplined home defence.
Aside from ambitious long-range efforts from Emerson Royal and Sarr, Conte's side appeared most capable of threatening from set-pieces but neither Kane nor Eric Dier were able to direct headers on goal from two excellent Son deliveries.
In the end, Spurs were grateful for the profligacy of the hosts as Belgian midfielder Charles de Ketelaere and German defender Malick Thiaw both headed excellent opportunities - to put the Italian side firmly in control of the tie - wide.
Had either nodded in from close range, Spurs would have faced an even more challenging recovery operation in the return leg in London on Wednesday, 8 March.
As it is, they must try to turn the tie round without Dier, who will be suspended after he collected a second-half booking.
Milan continue bounce back against Spurs
Prior to last Friday's victory over Torino, Stefano Pioli's side had endured a miserable start to 2023, picking up just two points from a possible 15 - and slipping to fifth in Serie A.
However, while they do not possess the star quality or swagger of the great Milan sides, they displayed plenty of know-how to carve out a slender lead.
Their only regret will be not to have put the tie beyond a Spurs side that competed well but barely laid a glove on them in the final third.
As it is, a place in the quarter-finals very much hangs in the balance, although Conte will still have to figure out a way to compensate for the loss of Uruguay international Bentancur, who has become a key player since arriving from Juventus just over 12 months ago.
The Italian will also demand greater diligence in defence from his side with Argentine Cristian Romero sure to come under scrutiny for his role in Milan's win.
The World Cup-winning centre-back was outjumped and left floundering by Hernandez in the build-up to the home side's goal and was later booked for an ill-timed challenge on the lively Rafael Leao.
Stopping the Portugal international's menacing runs in the second leg will be critical to Spurs' hopes as they bid to prevent Milan from reaching the quarter-finals for the first time since 2012.
Player of the match
GiroudOlivier Giroud
AC Milan
Squad number9Player nameGiroud
Squad number19Player nameHernández
Squad number20Player nameKalulu
Squad number24Player nameKjaer
Squad number8Player nameTonali
Squad number10Player nameDíaz
Squad number17Player nameRafael Leão
Squad number28Player nameThiaw
Squad number90Player nameDe Ketelaere
Squad number32Player namePobega
Squad number12Player nameRebic
Squad number1Player nameTatarusanu
Squad number30Player nameJunior Messias
Squad number33Player nameKrunic
Squad number56Player nameSaelemaekers
Line-ups
AC Milan
Formation 3-4-2-1
1Tatarusanu
20Kalulu24Kjaer28Thiaw
56Saelemaekers33Krunic8Tonali19Hernández
10Díaz17Rafael Leão
9Giroud
1Tatarusanu20Kalulu24Kjaer28Thiaw56SaelemaekersSubstituted forMessiasat 77'minutes33Krunic8TonaliBooked at 80minsSubstituted forPobegaat 86'minutes19HernándezBooked at 90mins10DíazSubstituted forDe Ketelaereat 77'minutes17Rafael LeãoSubstituted forRebicat 90+1'minutes9GiroudSubstitutes
2Calabria5Ballo-Touré12Rebic27Origi30Messias32Pobega46Gabbia83Mirante90De Ketelaere92NavaTottenham
Formation 3-4-2-1
20Forster
17Romero15Dier34Lenglet
12Emerson Royal4Skipp29Sarr14Perisic
21Kulusevski7Son Heung-min
10Kane
20Forster17RomeroBooked at 48mins15DierBooked at 63mins34LengletSubstituted forDaviesat 81'minutes12Emerson Royal4Skipp29Sarr14Perisic21KulusevskiSubstituted forRicharlisonat 70'minutes7Son Heung-minSubstituted forDanjumaat 81'minutes10KaneSubstitutes
6D Sánchez9Richarlison16Danjuma23Porro25Tanganga27Lucas Moura33Davies40Austin41Whiteman45DevineReferee:Sandro SchärerAttendance:74,320Live Text
Match ends, AC Milan 1, Tottenham Hotspur 0.
Second Half ends, AC Milan 1, Tottenham Hotspur 0.
Foul by Ivan Perisic (Tottenham Hotspur).
Pierre Kalulu (AC Milan) wins a free kick in the defensive half.
Theo Hernández (AC Milan) is shown the yellow card.
Richarlison (Tottenham Hotspur) wins a free kick on the right wing.
Foul by Theo Hernández (AC Milan).
Substitution, AC Milan. Ante Rebic replaces Rafael Leão.
Oliver Skipp (Tottenham Hotspur) wins a free kick in the attacking half.
Foul by Charles De Ketelaere (AC Milan).
Attempt missed. Eric Dier (Tottenham Hotspur) header from the centre of the box is high and wide to the right. Assisted by Ivan Perisic with a cross following a corner.
Corner, Tottenham Hotspur. Conceded by Simon Kjaer.
Substitution, AC Milan. Tommaso Pobega replaces Sandro Tonali.
Attempt missed. Ben Davies (Tottenham Hotspur) left footed shot from outside the box is high and wide to the left. Assisted by Oliver Skipp.
Hand ball by Malick Thiaw (AC Milan).
Offside, Tottenham Hotspur. Eric Dier tries a through ball, but Ben Davies is caught offside.
Attempt missed. Eric Dier (Tottenham Hotspur) header from the centre of the box misses to the right. Assisted by Ivan Perisic with a cross following a corner.
Corner, Tottenham Hotspur. Conceded by Pierre Kalulu.
Attempt blocked. Pape Sarr (Tottenham Hotspur) right footed shot from outside the box is blocked. Assisted by Richarlison.
Substitution, Tottenham Hotspur. Ben Davies replaces Clément Lenglet.