Milan held Tottenham to a 0-0 draw on Wednesday to preserve their 1-0 lead from the first leg and advance to the Champions League quarter-finals for the first time in 11 years.
Brahim Diaz's goal in the early stages of the reverse fixture gave Milan something to protect at Tottenham Hotspur Stadium and they did exactly that in a game of few chances.
Neither side managed an attempt on target in the first half and, while Spurs did show more urgency in the second period, there was not enough quality to break down Milan.
Spurs, who had Cristian Romero sent off 11 minutes from time for a second bookable offence, have now exited the Champions League and FA Cup in the past week.
Kick-off was delayed due to traffic congestion around the stadium and neither side truly turned up in the first half.
The onus was on Tottenham to find a goal but Emerson's deflected shot, which failed to test Mike Maignan, was the best they could muster and they were booed off at half-time.
Stand-in Spurs goalkeeper Fraser Forster was called into action early in the second period when keeping out Diaz's shot with his feet.
Maignan was finally required with 63 minutes played, but Pierre-Emile Hojbjerg's angled drive was simple enough to deal with.
Romero flew into a challenge on Theo Hernandez to receive a second booking, yet Harry Kane so nearly salvaged extra time when his header was superbly kept out by Maignan.
There was to be no late drama, though, with Divock Origi going closest to making the breakthrough on the day when hitting the post at the end of a late breakaway attack.
On this day in 2021: Spurs sack Jose Mourinho days before Carabao Cup final
Jose Mourinho was sacked as manager of Tottenham on this day in 2021, less than a week before he was due to lead them out for the Carabao Cup final.
Spurs’ Premier League form was what ultimately cost the Portuguese his job, with his last match in charge a 2-2 draw with Everton which left Tottenham seventh, five points off the Champions League places and with just one win from their last five league games.
Mourinho’s dismissal after just 17 months at the helm was announced hours after Tottenham had confirmed they intended to join a breakaway European Super League, plans that were swiftly aborted after fans’ backlash, although that was unrelated to the Portuguese’s axing.
The 58-year-old was denied the chance of delivering the club’s first piece of silverware in 13 years, with academy coach Ryan Mason put in caretaker charge as Tottenham lost 1-0 to Manchester City in the EFL Cup showpiece.
Spurs striker Harry Kane, whose form that season had been a bright spot with 47 goal contributions in 43 games, wrote on Twitter: “Thank you for everything Boss. A pleasure to have worked together. I wish you all the best for your next chapter.”
Tottenham chairman Daniel Levy spoke of his regret following Mourinho’s departure, having long coveted the former Chelsea and Real Madrid boss.
Levy said on the club’s official website: “Jose and his coaching staff have been with us through some of our most challenging times as a club.
“Jose is a true professional who showed enormous resilience during the (Covid-19) pandemic. On a personal level I have enjoyed working with him and regret that things have not worked out as we both had envisaged.
“He will always be welcome here and we should like to thank him and his coaching staff for their contribution.”
Mason remained steward until the end of the season before making way for Mourinho’s fellow Portuguese Nuno Espirito Santo, who had a disappointing four-month spell in charge
FC Halifax back in the play-off places after draw with Oldham
FC Halifax moved back into the play-off places in the National League as Adan George rescued a point in a 2-2 draw at home to Oldham.
The visitors took the lead in the 18th minute through Dan Gardner’s half-volley from a corner before Rob Harker levelled for the home side a minute into first-half stoppage time, smashing the ball home.
Oldham were awarded a penalty when Joe Garner was fouled in the box and Gardner restored Latics’ lead from the penalty spot in the 58th minute, but The Shaymen levelled again in the 72nd minute through substitute George’s smart finish from a narrow angle.
Halifax climb back into the play-off spots on goal difference where they are tied on 68 points with Aldershot, while Oldham remain 10th.
Aldershot move into play-off places with victory at 10-man Gateshead
Kwame Thomas headed Aldershot into the National League play-off places in a 1-0 win away to a Gateshead side who played almost half the match with a defender deputising in goal.
Gateshead had goalkeeper Nathan Harness sent off in the 47th minute for bringing down James Daly outside the box and, with no stopper on the bench, Louis Storey went between the posts for the rest of the night.
Storey made a good save to keep out Cian Harries’ free-kick in the 51st minute, but could do nothing as the visitors took the lead 10 minutes later.
Thomas got on the end of a looping cross from Josh Barrett to head in, and it proved enough for a win that puts them one point above FC Halifax, who host Oldham on Thursday.
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