At half-time, Mourinho went over New Manchester United's defensive responsibilities in detail. AC Milan's attack was extremely dangerous, with Pirlo directing play from deep while Rui Costa and Seedorf operated farther forward. That combination was the main reason Ancelotti's system with two advanced playmakers had been so effective in Serie A, and with all three players in good form, Mourinho's decision to field three central midfielders was specifically designed to deny Rui Costa and Seedorf the space they needed.
Mourinho's approach was straightforward: defend first, control the available space, and refuse to give Milan clean attacking positions. Kaká would continue pressing Pirlo, Drogba would occupy Nesta and Maldini, while Palacio stayed close enough to Milan's defensive line to threaten any space behind it. In midfield, the distances between the lines had to remain compact at all times.
Cafu's attacking ability on Milan's right also required special attention, so Mourinho instructed De Rossi to shade towards that side whenever necessary, while Essien and Beckham concentrated on limiting Rui Costa through the middle. The entire defensive structure depended on intelligent off-the-ball movement, and as the understanding between New Manchester United's midfielders had improved throughout the season, so had their ability to occupy space collectively.
That had already left several strong attacking teams frustrated against them, and Milan experienced the same problem in the second half.
Rui Costa and Seedorf were given very little room and struggled to provide meaningful service to the forwards. Pirlo was forced to start attacks with longer passes more frequently, but under pressure those balls naturally carried a higher risk than short combinations, which reduced Milan's attacking efficiency even further.
Kaká continued harassing Pirlo and even stole the ball from him once before releasing Palacio. The move was stopped by the assistant referee's flag, but had Palacio been allowed to continue, he might well have been through on goal.
Ancelotti paced repeatedly along the touchline. He had expected New Manchester United to cause problems, but he had not anticipated just how much the team had improved after more than half a season together. The difference was especially obvious in midfield. Compared with the UEFA Super Cup at the start of the season, Mourinho's side were far better at controlling space and closing passing lanes.
Ancelotti was not without options, however. Defending was about occupying space; attacking was about creating it. New Manchester United were currently controlling too much of the pitch, which meant Milan needed someone capable of opening spaces through individual quality. Fortunately for Ancelotti, one such player was sitting on the bench.
Rivaldo.
The problem was deciding who to remove.
Filippo Inzaghi was arguably Milan's best striker when space inside the penalty area became limited, while Shevchenko had not influenced the match greatly but was in exceptional form. Taking either off carried obvious risks.
Mourinho was thinking along similar lines. He knew Ancelotti would eventually change something. Fifteen minutes of the second half had passed, and although Milan's pressure looked intense, most of their danger still came from isolated moments rather than sustained control. Anyone watching closely could see how difficult they were finding it to create clear chances.
In the 63rd minute, Ancelotti finally acted. Rivaldo came on for Rui Costa, whose poor performance had clearly frustrated him. Rui Costa was visibly unhappy as he left the pitch, and Ancelotti went over to speak with him before sending Rivaldo on.
The substitution changed Milan's attack almost immediately. Ancelotti instructed his players to find Rivaldo more often. He had not relied heavily on the Brazilian that season because Rivaldo still preferred to solve situations individually, but that was exactly what Milan needed now. His technique and imagination could create space where the structure alone could not.
Rivaldo began causing problems almost at once.
Mourinho responded immediately. He decided to remove Kaká and introduce Yaya Touré, sending the Ivorian midfielder to warm up.
Before Yaya could enter, Milan scored.
In the 68th minute, Rivaldo received the ball on the right, escaped De Rossi's pressure, and advanced towards the edge of the penalty area. Without warning, he unleashed a fierce shot towards goal.
Čech had been fully focused, but the strike came so quickly that he could only react rather than set himself properly. He threw himself across goal and managed to parry the ball, but could not hold it.
As Čech hit the ground and tried to recover, a red-and-black shirt appeared in front of him.
Filippo Inzaghi.
He had started moving the instant Rivaldo struck the shot, gambling on a rebound before anyone else had reacted. When the ball spilled loose, Inzaghi was already there to tap it into the empty net.
1-0.
San Siro erupted.
"Super Pippo!"
The chant rolled around the stadium. Inzaghi had rescued Milan repeatedly at important moments that season, and once again he had produced a goal when they needed one most.
Mourinho threw out his arms in frustration and kicked at the turf. His anger was obvious, but it was not directed at any particular player. There had been no clear individual error. Even Čech's failure to hold the shot was understandable given how suddenly and powerfully Rivaldo had struck it.
Curtis might have reacted sooner to Inzaghi's movement, but even that was difficult to criticise too heavily. Inzaghi had begun anticipating the rebound at the very moment Rivaldo pulled back his leg.
Mourinho turned towards Cassell with a grimace.
"That bastard really is a fox in the box."
Cassell could only smile ruefully. It was an infuriating goal to concede, but not an inexplicable one.
Before the match, Mourinho and his staff had already discussed the worst-case scenario: how to prevent the tie from collapsing if Milan seized control the way they had in the UEFA Super Cup. From that perspective, conceding only once at San Siro was hardly disastrous.
Nobody inside New Manchester United would say that aloud, of course. The standards of the club had changed. Whatever the circumstances, winning remained the objective.
Yaya Touré had finished warming up by then and approached the technical area with a slightly uncertain expression.
"Boss, am I still going on?"
Mourinho nodded immediately.
"Of course. And when you get out there, stay close to that Brazilian. Don't let him enjoy himself."
Yaya nodded.
His introduction tightened New Manchester United's midfield again. Milan tried to increase the pressure, but their attacks repeatedly broke down, while Rivaldo became much quieter once the space around him disappeared.
Without Kaká, New Manchester United simplified their counter-attacking approach. Drogba became the primary target for direct passes, using his strength to compete for the first ball and bring Palacio into play around him. The strategy caused Milan occasional problems, although Nesta and Maldini continued to defend well overall.
Ancelotti, however, was clearly not satisfied with a 1-0 home victory. He wanted a larger advantage before travelling to Manchester, so he made another attacking change and replaced Pirlo with Danish striker Jon Dahl Tomasson.
Pirlo's performance had been subdued. Several of his better passes had not been converted by the forwards, and once New Manchester United increased the pressure around him, he had found it increasingly difficult to influence the match.
The purpose of Tomasson's introduction was obvious.
Milan wanted another goal.
Shevchenko, Inzaghi, Rivaldo, and Tomasson began attacking New Manchester United's defence in waves. Mourinho's players, however, refused to break. They defended with discipline, won headers, blocked passing lanes, and survived every late surge until the referee finally ended the match.
AC Milan 1-0 New Manchester United.
At the post-match press conference, several Italian journalists questioned Mourinho about his conservative approach. He responded with a faint smile and immediately pointed to the statistics from the opening half-hour, when New Manchester United had produced twelve shots and repeatedly threatened Dida's goal.
Mourinho nevertheless acknowledged Milan's quality and rejected the suggestion that the tie was over.
"One-nil is one of the most dangerous scorelines in football," he said. "Milan wanted more goals tonight, especially at home, but my players stopped them from getting them. Given the circumstances, this is a result we can work with, and I'm very satisfied with the performance. When we return to Manchester, we'll show Milan an even better version of ourselves."
"Our tactical plan worked both early in the match and later when we defended deeper. Milan simply have outstanding players. Rivaldo shoots from distance, Inzaghi reacts to the rebound, and suddenly there's a goal. Sometimes football is that simple. I'm not blaming any of my players for it because they did their jobs very well."
There was none of Mourinho's usual bitterness after defeat. He was calm, almost relaxed, as though the result had fallen within the range he had expected.
Ethan understood why.
During their preparations, Mourinho had never been especially optimistic about winning at San Siro. Beating AC Milan away from home in a two-legged European tie was an enormous challenge. His preferred outcome had been a draw; if that proved impossible, then the priority was keeping the deficit manageable.
Mourinho had even considered the possibility of losing by two goals because Milan's attack was among the strongest in Europe and their defence was built around Nesta and Maldini. Against an opponent of that quality, expecting to dominate San Siro would have been unrealistic.
That was why Ethan remained in good spirits despite the defeat.
After watching the match with Berlusconi, he accepted an invitation to dinner in Milan. During the meal, Ethan invited Berlusconi to Manchester for the second leg and made no attempt to hide his confidence that New Manchester United could overturn the deficit at Old Trafford.
Berlusconi accepted.
The conversation then moved on to cooperation between the clubs, including the Goal! film project, charity initiatives they had previously supported together, and several longer-term plans. By the end of the evening, the two men had reached broad agreement on a number of areas.
Among club owners and chairmen in European football, Ethan had already built an unusually strong network. New Manchester United might have been in their first Premier League season, but they maintained good relationships with AC Milan and Real Madrid and even closer ties with clubs such as Benfica, Genk, and Ajax.
As the team's performances improved, so did its standing within European football.
Ethan had always believed that becoming a major club required more than money or trophies. Recognition from peers mattered as well. A club needed sporting credibility, institutional respect, and relationships that extended beyond the transfer market.
Chelsea could buy stars. Manchester City might one day spend heavily too. But Ethan wanted New Manchester United to build something harder to acquire.
Respect.
Of course, respect ultimately depended on results.
The second leg against Milan therefore became a major focus for both the club and its supporters, but the congested schedule forced Mourinho to make difficult choices elsewhere. In the end, he prioritised the UEFA Cup, and New Manchester United paid for that decision with a setback in the league.
Fortunately, when AC Milan finally arrived at Old Trafford, Mourinho's side looked sharp from the opening whistle.
(To be continued.)
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