This achievement is pretty hard to do but not impossible to get. It took my several attempt to obtain this achievement. Below is what I did.
I started by playing in the Memorial cup played every single game that I could and won the Cup. I was drafted and played my first season.
My first season was played without skipping/simulating games. Their are some games you can’t win even if you tried too but I believe you are destined to loose the games and win the games they want you to win. I ended up in 5th position with a record of 29-43-8. I did not make it to the playoffs.
During the season you will get dropped to a different team from a different league and will get transferred back to your team after about 10 games later
My 2nd season I simulated every single game until the last game of the season which I tried to win but somehow lost the game since you are in and out of the game several times. My record was better my second season than my first with a record of 35-33-12 I don’t know how but I did not make it to the playoffs and my position was still 5th.
My 3rd season was very different from the first 2. I played it very differently and was careful how to do it. I played 15 games simulated 10 for the whole season. I did better doing it this way with a record of 55-21-6. My position on the table was 1st place in my division. I made it to the playoffs where I played 3 games and simulated 3 to see if I got the 4th win those times which I did. I did the same for the rest of the games until I reached the Stanley Cup Final and I won and as soon as I won the achievement popped up.