The Champions League Semi-Finals start today with a heavyweight matchup between Real Madrid and Bayern Munich. Since Manchester United is long gone in this competition, let’s reminisce about the good old days. On the road to the final in 1999, Manchester United faced stiff competition from Juventus. Below, we take a look at how that matchup played out.

First Leg

Manchester United were given the first leg at home and had a chance to set the tone for the tie. Unfortunately, it did not quite go to plan for Sir Alex Ferguson’s side.

In the 25th minute, Juventus captain Antonio Conte put the visiting side ahead 1-0. Conte slipped in behind the United defense and found the far corner for an all-important away goal.

United created chance after chance in the match yet were unable to find the back of the net. Jaap Stam, Roy Keane, and Paul Scholes forced good saves, and the Reds had a goal ruled out due to an offside.

Finally, though, Manchester United found a breakthrough in the 92nd minute. Juventus failed to clear the ball, and after some pinball in the box, the ball fell to the left foot of Ryan Giggs, who smashed the ball into the roof of the net.

What would a match involving Sir Alex Ferguson be without some late drama?

Second Leg

After drawing 1-1 at Old Trafford, Sir Alex Ferguson’s side knew that progressing would be difficult. The situation became all the more challenging when Filippo Inzaghi scored twice in the opening eleven minutes to give Juventus a 3-1 lead in the tie.

In the 24th minute, captain Roy Keane pulled one back to bring Manchester United back into the tie. Keane flashed across the front post and flicked a brilliant header into Peruzzi’s net to restore a sense of belief in Ferguson’s side.

Ten minutes later, Dwight Yorke brought United level in the match but ahead in the tie. Andy Cole picked up the ball at the edge of the box and played in a beautiful ball to the back post that Yorke headed down into the net. This was Yorke’s 8th goal in the 98/99 UCL, which tied him with Andriy Shevchenko for the competition’s Golden Boot.

After attack after attack and yellow card after yellow card, Manchester United got the dagger through Andy Cole. Dwight Yorke split two Juventus defenders before being taken down by Peruzzi. Instead of immediately giving the penalty, the referee played on, and Andy Cole tapped the ball in to make it 3-2 United and put the game out of reach for Juventus.

As the final whistle blew, a huge smile spread across the face of Sir Alex Ferguson. Ferguson singled out one performance against Juventus after the tie. When speaking about Roy Keane, he said:

“Pounding every blade of grass, competing as if he would rather die of exhaustion then lose, he inspired all around him, I felt as if it’s an honor to be associated with this player.”

Keane scored the goal to renew confidence for United in the first half and fought every moment in a true captain’s performance, where, of course, he also picked up a yellow card.

The 1999 Semi-Final against Juventus was legendary, with United fighting back time after time to book a place in the Champions League Final. We all know how the story ends, as Manchester United came from behind yet again, this time to take home the title in Barcelona. Will Manchester United ever reach these heights again?