This achievement is for winning all 9 possible online cups. Only 1 cup is open per weekend (5PM Friday - 10AM Monday) This is GMT.
So this achievement is only possible after 9 weeks of playing the game.
To access online cup mode go to Xbox live > Street Season > Cup match. I reccomend having a 90+ rated team and at least some experience of playing the game online before attempting to win a cup. If not this will prove to be very frustrating, as there are some good players around, especially when you get to the Semi-final/Final.
To see which cups you have won go to Street Stories in the Street Season menu then click on Trophies. Im not sure what order the the cups will go in, but i assume that they will cycle round in the same order if you miss one.
Edit: I can confirm that they will go in the same order as the next one after the 9th cup has finished is the dutch invitational, which was the first one.
From what i can figure the order so far is like this:
Dutch invitational cup
Uk street cup finals
Tokyo futsal cup
Annual street 5's championship
6 a side elimination challenge
European futsal invitational
Canal classic 5 a side tournament
New York 6's tournament of champions
South american futsal championship
Tips :
• Have a 90+ rated squad with a keeper with Max goalkeeping ability.
• Check the oppositions rating before you ready up because if its considerably higher than yours it's a good idea to quit.
• Don't worry about doing skill as it's much more effective to do lots of passing and sprinting past players. But on a side note, little bits of skill to beat the lone player or score can be very good if you are familiar with using it. Otherwise don't bother.
• When defending don't go running in to tackle them when they are near your goal. It's much more effective to just stand off them until they make a move and then try and get the tackle in. When you are doing this though, don't stand too far off as this will allow them to shoot.
• It works best for me to play the formation where there is the most forwards. As this allows you to score lots of rebounds and there is usually a player for you to pass across goal to score some easy tap-ins.
• Have one defending player which has max defending and good speed as these players can be life savers.
• Keep trying, no matter if you keep losing, eventually you will get some weaker opponents and hopefully be able to win.
• And lastly, Good luck. You'll need it.
Today it is currently possible to have won 9 cups.
It is not possible for anyone to have won this achievement legitimately before 11th May 2012, or offline. Therefore anyone that does, has Hacked/Cheated/Glitched. Also if the person has won this achievement on a Tuesday, Wednesday or Thursday, it is another indication that they have illegitimately won this achievement. (Please consider time zones before reporting someone for this).
I only say this as there has been some problems with hackers on this achievement.