Rio Ave qualifying for the Europa League group stage would be one of the greatest achievements in Portuguese football history
Rio Ave caused a major upset in the Europa League third qualifying round by defeating Turkish giants Besiktas on penalties - but an even bigger test awaits them in the coming round.
Though going into the clash with Besiktas as clear underdogs, particularly as the away side, Rio Ave were highly impressive throughout the game, and though they rode their luck at times, created enough opportunities and genuine goalscoring opportunities to score a few themselves.
They were then the side to hold their nerves on penalty kicks, and advance to the Europa League play-off round - just one match from the group stage.
And the prize for winning the one-off match against Besiktas is the chance to welcome Italian giants AC Milan to Vila do Conde, an incredible opportunity for Rio Ave to test themselves against one of the very best sides in the world.
It also comes with a hint of misfortune, though. Rio Ave, if you would believe it, were actually the seeded side for the draw due to their victory over Besiktas - and so the fact that they were drawn against AC Milan, surely indisputedly the hardest possible unseeded side, is incredibly unfortunate and completely diminishes their chances of making the group stage. But it is an opportunity that doesn’t come around too often.
Rio Ave knew that they were going to be drawn against one of AC Milan, Hapoel Be’er Sheva, or CSKA Sofia - and unfortunately for them - or fortunately depending on how you look at it - the former Champions League winners were the side they were paired with.
To come out on top against Besiktas in a one-off match is a quite stunning achievement - but to now have to follow that up with a match against AC Milan ensures that should Rio Ave somehow find a way to get through, it will be one of the greatest ever achievements in Portuguese footballing history.
Previously, Rio Ave have only reached the Europa League group stage on one occasion, their one and only showing in the tournament proper coming in 2014, defeating modest Swedish duo IFK Goteborg and IF Elfsborg to get there - not quite as challenging as the two fixtures they have been handed this time around.
When they reached the group stage in 2014, they ended up finishing 4th in a group containing Dynamo Kiev, Steaua Bucharest and Aalborg BK, finishing with just 4 points overall.
Since then, they have reached the qualifying stages on two occasions, but failed to make it past the first round either time, losing to Slavia Prague on away goals in the third qualifying round in 2017, before being defeated by Polish outfit Jagiellonia Bialystok 4-5 on aggregate after a fascinating 4-4 draw at home in the second qualifying round.
If they overcome AC Milan on Thursday, it will therefore go down as one of the greatest achievements in history - not only in Portugal, but perhaps in continental terms too.
