The second leg of the 1998–99 UEFA Champions League semi-final between Juventus and Manchester United was a football match that took place at the Stadio Delle Alpi in Turin, Italy, on 21 April 1999. Manchester United won the match 3–2; combined with a 1–1 draw in the first leg, that gave them a 4–3 aggregate win and sent them to the 1999 UEFA Champions League Final.
Having gone 2–0 down to early goals from Filippo Inzaghi, the win is often described as one of Manchester United's greatest ever. It is particularly notable for Roy Keane's performance, often described as one of the best individual performances in a football match ever; Keane scored United's first goal, sparking the comeback. Dwight Yorke scored Manchester United's equaliser, before Andy Cole scored the winning goal late in the game.
Background
Manchester United were aiming to be the first English club to reach the European Cup / Champions League final since Liverpool in 1985. Juventus had been one of the strongest teams in European football during the 1990s; they had reached the Champions League final in each of the previous three seasons, winning the tournament in 1996. United had played Juventus in the 1996–97 and 1997–98 seasons of the Champions League; the Italians had won three of these meetings (all 1–0) and United won the other by a 3–2 score.
The first leg of the tie, played at Old Trafford in Manchester, was dominated by Juventus but ended in a 1–1 draw; Antonio Conte scored an early goal for Juventus that was matched by a late equaliser from Ryan Giggs.
This meant that whichever team won the second leg would advance to the 1999 UEFA Champions League Final, and Juventus, with home advantage, were strong favourites to do so, United veteran George Best saying the team needed "a miracle." Under the away goals rule that applied at the time, Juventus would also advance if the second leg ended 0–0; if it was 1–1, the tie would go to golden-goal extra time and possibly a penalty shootout; if it was 2–2 or a higher-scoring draw, United would advance.
Under the competition's rules at the time, a player who received two yellow cards in that season's tournament at any point would be suspended for one game. Twelve players in the matchday squads had received yellow cards earlier in the season and would be suspended for the final if they were booked in this game and qualify: Denis Irwin, Ronny Johnsen, Roy Keane, Paul Scholes and Phil Neville for United; Antonio Conte, Didier Deschamps, Edgar Davids, Angelo Di Livio, Zinedine Zidane, Paolo Montero and Angelo Peruzzi for Juventus.
Route to the semi-final
Juventus
As winners of the 1997–98 Serie A title, Juventus qualified for the 1998–99 UEFA Champions League group stage automatically and were placed into Pot 1 for the draw, along with title holders Real Madrid and the domestic champions of Germany, Spain, France and the Netherlands: Kaiserslautern, Barcelona, Lens and Ajax. They were drawn into Group B along with Spanish club Athletic Bilbao, Norwegian side Rosenborg and Galatasaray from Turkey.
After five straight draws – a Champions League record at the time – Juventus went into the final matchday needing to beat Rosenborg at the Stadio Delle Alpi and hope that Galatasaray lost to Athletic Bilbao at San Mamés. First-half goals from Filippo Inzaghi and Nicola Amoruso gave Juventus the victory they required, while Athletic's Julen Guerrero scored the only goal in the other game. That left the top three teams level on eight points; their order was determined by their head-to-head record, and since Galatasaray and Rosenborg had beaten each other in their matches on Matchdays 3 and 4, the three teams were separated by Juventus' final-day victory over the Norwegians. That made Juventus the first club to reach the Champions League knockout phase without winning any of their first five group matches.
Juventus were paired with Group A winners Olympiacos in the quarter-finals. A 2–1 win at the Stadio Delle Alpi in the first leg gave Juventus the advantage thanks to goals from Inzaghi and Antonio Conte; however, a late penalty from Andreas Niniadis meant Olympiacos only needed to win 1–0 in Athens to go through on the away goals rule. Siniša Gogić scored in the 12th minute to give the Greek side the scoreline they needed, but Conte scored in the 85th minute to make it 1–1 and send Juventus through with a 3–2 aggregate win.