Edit- It seems that you an just buy 2 wins and you will get the achievement.
The easiest way to do this is to go to your football club catalogue and buy a win a road to rio and a draw a road to rio. The reason is because you need 5 pints to advance through the first city. Now go and play your last match(you have 4 points already). Win or tie and the achievement will pop. Just to add you must play the last math for the achievement to unlock.