26 May 1993 - A Hill Too High To Climb

On 26 May 1993, São Paulo repeated as Copa Libertadores champions despite losing the second leg of the final to Universidad Católica, 2-0.

The Brazilians won the tournament for the first time in 1992, beating Newell's Old Boys on a penalties. For the 1993 final, they did their best to prevent going to another shootout, winning the first leg against Católica by the score of 5-1 (including an own goal by Católica defender Daniel López). The Chileans' only goal that day was a penalty kick by forward Juan Carlos Almada (pictured) in the 85th minute.

In the second leg, played at the Estadio Nacional in Santiago, Católica did their best to overcome the deficit, going up 1-0 with a 25-yard blast from midfielder Ricardo Lunari in the 9th minute that beat the keeper to the top corner. Then, just six minutes later, the referee awarded a penalty kick to Católica and Almada again converted. The keeper, diving to his right, did well to get a hand to it, but the shot was too strong.

Despite the rapid 2-0 lead, that would prove to be day's last goal, as São Paulo clamped down on defense and prevented Católica from narrowing the aggregate margin any further. It remains Católica's only appearance in the final, while São Paulo went on to win it for a third time in 2005.

22 December 2011 - School Lets Out For Universidad de Chile

On 22 December 2011, a loss to Católica ended Universidad de Chile's unbeaten streak at 36. But they consoled themselves with their second of three straight league titles.

UDC, who won the 2011 Apertura Final over Católica the previous June, last lost on 13 July, falling 0-2 to Magallanes in the Copa de Chile. Afterward, they went on a tremendous run that included the Copa Sudamerica, which they won over LDU Quito on 14 December to extend their unbeaten run to 35 games in all competitions, bettering their 33-game streak from 1999. For their 36th game, they beat Católica 1-2 in the first leg of the 2011 Clausura semi-finals on 18 December, then hosted Católica for the second leg four days later.

After conceding a 42nd-minute goal to Católica's Kevin Harbottle, UDC drew level with a strike from Osvaldo González in the 59th minute. The game remained 1-1 until stoppage time, when José Luis Villanueva scored for the visitors to set the final margin as a 1-2 win for Católica.

Although the goal put the two teams levels on points and goal differential, UDC still advanced by virtue of having finished higher than Católica in the classification phase. They went on to defend their title successfully, beating Cobreloa in the final, then defended it again in the 2012 Apertura.

22 May 1969 - A Little Easier The Second Time Around

On 22 May 1969, Estudiantes won their second Copa Libertadores, beating Nacional 2-0 in the final's second leg.

The Argentinians had won the previous year's tournament, but it had taken them sixteen matches to do it, including a three-match final against Palmeiras that Estudiantes won in a replay. But as holders, they received a bye into the 1969 semifinals, where they won both games against Universidad Católica by identical scores of 3-1 to reach the final.

There, they faced Nacional, who had reached the final twice before, but lost to Argentinian teams both times (Independiente in 1964 and Racing in 1967). They played a full thirteen-game schedule to get there a third time, giving them a distinct disadvantage against the well-rested Estudiantes side.

Nacional hosted the first leg in Montevideo on 15 May and lost 0-1 to a 66th-minute goal from Eduardo Flores. In the second leg in La Plata one week later, Flores scored again to put Estudiantes up 1-0, then Marcos Conigliaro stretched the margin to 2-0 in the 37th minute and complete the victory.

Estudiantes went on to win the competition again in 1970, becoming the first team to lift the trophy in three consecutive years.

26 May 1993 - A Hill Too High To Climb

On 26 May 1993, São Paulo repeated as Copa Libertadores champions despite losing the second leg of the final to Universidad Católica, 2-0.

The Brazilians won the tournament for the first time in 1992, beating Newell's Old Boys on a penalties. For the 1993 final, they did their best to prevent going to another shootout, winning the first leg against Católica by the score of 5-1 (including an own goal by Católica defender Daniel López). The Chileans' only goal that day was a penalty kick by forward Juan Carlos Almada (pictured) in the 85th minute.

In the second leg, played at the Estadio Nacional in Santiago, Católica did their best to overcome the deficit, going up 1-0 with a 25-yard blast from midfielder Ricardo Lunari in the 9th minute that beat the keeper to the top corner. Then, just six minutes later, the referee awarded a penalty kick to Católica and Almada again converted. The keeper, diving to his right, did well to get a hand to it, but the shot was too strong.

Despite the rapid 2-0 lead, that would prove to be day's last goal, as São Paulo clamped down on defense and prevented Católica from narrowing the aggregate margin any further. It remains Católica's only appearance in the final, while São Paulo went on to win it for a third time in 2005.