San Lorenzo will have to wait at least another year to break its jinx in the Copa Libertadores after a 2-0 defeat to San Luis of Mexico on Wednesday confirmed the Argentine side's elimination from the tournament and led to Miguel Angel Russo's resignation as coach.
Meanwhile, an away victory for Palmeiras in the all-Brazilian clash with Sport Recife complicated matters even further in Group 1, while Argentina?s Estudiantes and Universidad de Chile also registered important wins.
Experienced coach Russo paid for the loss in Mexico with his job after the Argentine club again fell short in the Copa Libertadores.
"I spoke with (San Lorenzo president Rafael) Savino and told the players. Football is like that, things like this happen. That?s it, I wish San Lorenzo all the best,'' Russo told Fox Sports after the match.
San Luis' slim chance of qualification now rides on beating already-qualified group leader Libertad and hoping San Lorenzo beats Universitario of Peru in the last round of matches. The Mexican club also needs a three-goal swing in goal difference to pip the Peruvians to second place.
Jesus Palacios crowned a tireless performance in the midfield for San Luis with the opening goal from a Noe Maya cross after 43 minutes.
Both clubs knew anything other than a win would mean elimination, but San Luis reacted to the pressure better in the second half. Jose Reyes headed home to give the Mexican club a two-goal cushion after 67 minutes and San Lorenzo then folded weakly.
Russo won the title with Boca Juniors in 2007 but failed to have the same instant impact at San Lorenzo, the only member of the so-called "big five'' Argentine clubs not to have won the Libertadores.
Both clubs were reduced to ten men at the end of the first half when San Lorenzo's Nestor Silvera and San Luis defender Omar Monjaraz were sent off after clashing on the edge of the San Luis box.
In Group 5, Cruzeiro lost its way in more ways than one after the Brazilian's team bus took a wrong turn on the way to the stadium to face Estudiantes, delaying kick off by 30 minutes.
The Cruzeiro players had to take to the field without warming up properly and produced a disjointed performance in a 4-0 loss.
The Brazilian club stays top of Group 5 with 10 points, but Estudiantes is now just one point behind. Deportivo Quito of Ecuador follows with five points, while Universitario of Bolivia eliminated by the Estudiantes win - has one.
Gaston Fernandez took advantage of Cruzeiro?s shoddy attempt at an offside trap after five minutes, pulling the ball back for Juan Sebastian Veron to opened the scoring for Estudiantes.
Fernandez then chipped over Fabio for the second goal after 32 minutes when Marquinhos gave the ball away in defense. Substitute Cristian Sanchez notched a double to bury the Brazilians with goals after 74 and 78 minutes, both strikes set up by Veron.
Keirrison and Diego Souza scored the goals that gave Palmeiras a vital away win in Group 1 over Brazilian compatriots Sport Recife.
At the group's half way stage, Palmeiras moved level on three points with defending champion Liga de Quito, with Sport and Colo Colo of Chile leading the way on six points.
Keirrison finished from close range after 23 minutes following a shot by Mauricio Ramos and Souza left defenders in his wake before finishing over goalkeeper Magrao after 72 minutes.
In the day's final match, Universidad de Chile dismantled Colombia's Boyaca Chico with a 3-0 home win. Goals from Emilio Hernandez after 21 minutes, Juan Manuel Olivera after 47 minutes and Nelson Cuevas in stoppage time sealed the victory.
The three points allowed the Chilean club to leapfrog Chico into second place in Group 7.
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