Football Manager 2020

It would appear this has been patched and is now obtainable. Whilst LuckyKant's method may work for only winning one match. It now works simply by meeting requirements. Please note though I am using version 20.4.1. Your game may need updated as earlier versions may not be patched. Here's how to get it

Select Fantasy Draft at main menu --> Create Draft. Next choose knockout cup and put two legged ties off to make this take half as long. Other settings can be whatever you want --> Create competition

Once competition loads create your manager and team. I always set my manager to the highest level of experience but not sure it matters.

On the next screen go to Add Manager --> Add AI Club. Then pick any AI team from the list. Then begin draft.

The thing about the draft is you have the ability to pick 25 players but since we are just playing 1 legged matches I just pick about 13 and blow my budget as I don't need the strength in depth. You can pick whoever you want but remember we are looking to win. To make things a little easier here is my squad I used which won about 85-90% of the matches

Note I usually play using a certain tactic which can be downloaded here
https://fm-base.co.uk/resources/fm20-4-1-beowulf-442-p104-ec...

This team fits that tactic well. If you are not sure how to use custom tactics find the Sports Interactive folder on your PC (for me it is under Documents) then go Football Manager 2020 --> gamepass --> tactics and save the tactic file in there. In game when on the team select screen go to the drop down menu next to tactics and hit load. The file should be there.

Anyway my team was

GK - Marc-Andre Ter Stegen
DL - Andrew Robertson
DC - Virgil Van Dijk
DC - Jerome Boateng
DR - Trent Alexander-Arnold
ML - Thomas Lemar
MC - Toni Kroos
MC - Arturo Vidal
MR - Riyad Mahrez
SC - Lionel Messi
SC - Leigh Griffiths

Note that Messi or Ronaldo always get picked first so if the AI takes one, then you take the other.

After that I just select a few versatile subs with the remaining cash.

Next up make sure that the tactic is set and then go to Actions on the home screen and select go on holiday. Be sure to select "use current match tactics" and "go on holiday indefinitely".

After each competition you will get a pop up with an option to start new competition. Just hit that and then rinse and repeat until you have won 25 times. With the tactic above and the team I selected I won about 8-9 out of 10 times. It does pop the achievement whilst you are on holiday. To check your progress go to the leaderboards from the menu in the bottom left and select Fantasy Draft from the drop down menu and then Knockout Cup Champion Points but note to get the leaderboard to refresh I had to restart the game and for some other weird reason, for me it only shows the first page of players (top 20), so you need to get onto that page for it to show your progress, lowest is currently 6 wins.

Also two other things to note - This does NOT need to be done with one team or on one save. I used multiple different teams to get my 25.

Second for some bizarre reason whilst writing this guide and checking things I completely lost the ability to go on holiday, the option wasn't even there. Despite multiple loads of the save it just wasn't giving me the option. To fix it, I closed the game, deleted all saves and then started again. It worked fine after that,

Finally matches played whilst going for this do count towards 100 Club

Edit: So, there is a workaround to unlock this.

Remove all your save files from the games folder. (Sports Interactive > Football Manager 2020 > Gamepass > Games). Move them to a new folder on the desktop. This may not be needed and it may unlock after completing the next game. I advise removing the save files if you were at 25 Cup Wins before the update. If you haven't done it, please follow Yurgi Windu's excellent guide.

Set up a Knockout Cup with two teams, one-legged. Get a friend to join.

Create a new manager and a new team.

Skip all picks and then win the game. The loser should mess around with their tactics, put a goalkeeper in goal and move the centre-backs out of the way.

Popped after the game. I had won 61 games before but it did not unlock for my partner who had only won 5 cups. He also hosted.

This will need more feedback and testing, please comment below what does and does not work.
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This achievement is currently unobtainable. I have won 44 cups as per the leaderboard. It seems that the achievement pulls data from your record (image is posted in the forum link below). My win record is 0% wins, 0% draws and 0% losses, with 0 titles/cups. That is obviously wrong.

I have reported it to Sports Interactive. This is how I worked with the devs to get the fixes last year. Please post in that forum to help get a fix ASAP.

https://community.sigames.com/topic/518844-game-pass-bugs/