Defending the Copa Libertadores title hasn’t been done since Boca Juniors in 2001 and it won’t be achieved this year after Racing Club stunned champions Flamengo at the Maracanã on Tuesday.

La Academia could consider themselves unfortunate not to win last week in Avellaneda but a change of fortune in Rio de Janeiro saw the home side squander a host of opportunities before Racing sealed a famous win from the penalty spot.

Injury to last season’s top scorer Gabriel Barbosa had given Racing a boost before kick-off and Vitinho in particular proved unable to fill Gabigol’s boots with a series of missed chances during a dominant opening period.

Racing knew that a single goal would change the tie and were patient in their approach until the game turned just after the hour mark. Flamengo’s defensive problems since the sale of Pablo Mari have been well documented and Rodrigo Caio’s clumsy sending off opened the door for Racing. Central defensive partner Gustavo Henrique held it ajar a little longer and his error moments later allowed Leonardo Sigali to poke Racing in front.

The ten men of Flamengo needed a goal to force penalties but were unable to find any way past the huge presence of Gabriel Arias in the Racing goal. That was until deep in stoppage time when Willian Arão flicked a corner inside Arias’ far post to send the tie to spot kicks.

The in-form Arias against the penalty expert Diego Alves. Or at least that was how it was billed. Racing were perfect from the spot and when Arias saved from injury time hero Willian Arão it was left to Fabricio Domínguez to score La Academia’s fifth sealing a historic victory.

After a difficult few weeks at the club a place in the Libertadores quarter-finals is the perfect tonic. Boca Juniors or Internacional lie ahead but after eliminating Flamengo nothing will concern Sebastián Beccacece’s side.

For River Plate it was a little more straight forward though their profligate finishing did make the last 16 clash with Athletico Paranaense a little more nervy than it should have been.

After the 1-1 draw in Curitiba last week the tie was still in the balance and as River continued to waste opportunities Marcelo Gallardo cut a visibly uncomfortable figure on the touchline.

When River did find a way through they found 21-year-old reserve goalkeeper Bento in inspired form and if Athletico had perhaps had a little more quality in attack they could have found a way to punish their hosts.

Ultimately seven minutes from time River found their goal. Rafael Santos Borré was bundled over in the box and Nicolás De La Cruz broke the deadlock after his initial penalty effort came back off the post.

A single Athletico goal would have forced penalties but never really looked likely to come so River held on to book their place in the quarter-finals once again. Independiente del Valle or Nacional will be up next and Gallardo will know that his side must improve if they are to go one better than last year.