AC Milan’s Bosnian midfielder Rade Krunić (left) and Tottenham Hotspur’s English striker Harry Kane contested the ball during the UEFA Champions League round‑of‑16 first‑leg match at the San Siro on 14 February 2023. (Photo by Marco Bertollo/AFP)
AC Milan progressed to the Champions League quarter‑finals for the first time since 2012, holding 10‑man Tottenham to a 0‑0 draw and winning the tie 1‑0 on aggregate. Tottenham’s European elimination came on the heels of an FA Cup exit, extending the club’s 15‑year wait for a trophy by at least another season.
Antonio Conte’s return to the touchline did little to spark his side. Tottenham were toothless in attack and played the final 12 minutes with ten men after Cristian Romero was sent off for two bookable offences. Kick‑off was delayed by ten minutes due to traffic congestion, and the match itself took even longer to get going. Conte, back after recovering from gallbladder surgery, was his usual animated self and received a yellow card from referee Clément Turpin for protesting a booking given to Clément Lenglet. Nevertheless, his players lacked energy, and Spurs failed to rise to the occasion.
Milan created the only moment of real imagination before the break when a well‑worked free‑kick found Junior Messias, whose shot went wide. Tottenham, having lost four of their previous six games—including a defeat to second‑tier Sheffield United in the FA Cup—could not hide their frustration, and the half‑time whistle was met with a smattering of boos from the home crowd. Conte could not provoke a response at the break, and Tottenham had to rely on stand‑in goalkeeper Fraser Forster to keep them in the tie.
Brahim Díaz scored the only goal of the first leg; his jinking run inside the Spurs box lacked the finish as Forster’s outstretched leg deflected the ball to safety. Spurs forced Mike Maignan into a save 25 minutes from time, tipping over Pierre‑Emile Hojbjerg’s strike. In the final 20 minutes, Conte switched to a front four—Richarlison joining Harry Kane, Dejan Kulusevski and Son Heung‑min—but there was little service for Kane, and hope of a Tottenham fightback vanished with Romero’s red card. The Argentine, often walking a fine line with discipline, received his third career red for lunging at Theo Hernandez.
Kane came closest to an equaliser when his header from a Son free‑kick was well saved by Maignan low to his right in stoppage time. Milan could have sealed victory on the night as well as on aggregate, but Sandro Tonali squandered a chance by shooting when teammates were in support, and Divock Origi’s effort struck the inside of the post. In the end, the seven‑time European champions held firm, ending more than a decade of waiting to reach the last eight. (AFP)
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