NHL 20

This is very simple.
Start a franchise, settings don't matter. Once in, go to team management, then assign scout.
From here, look at the first scout's region in the middle of the table. Press Y, select North America, CHL, and select one of the three locations. But of course not the one he's already in.
It should pop after you confirm his travel expense

- Start New Franchise (Any Settings are fine)
- Press to go to the Team Management Tab
- Go down to "Assign Scout"
- Press to Change Region
- Select North America
- Select CHL (Canadian Hockey League)
- CHEEVO UNLOCKED🏆
Video Guide:

This achievement is fairly straightforward and I have nothing to add to Kabobles' solution, but I thought I would also add more details because I got this achievement and all the other Franchise Mode achievements in my first try/season as the 32nd Franchise. This is how I did it:

I followed Jon Clink 96's Cup Champs solution and I edited the rosters to remove all the 85+ OVR players from each NHL team before starting franchise mode by moving them all into free agency. I also moved over all the 85+ OVR Alumni players from the Alumni All-Star team to really bolster the free agency options.

Now take note of the Top 5 Goalies, Top 15 Defensemen, & Top 30 Forwards by OVR (total of 50 players). These are your chosen 50, you'll need them later.

I then moved a bunch of 40-60 OVR players from other leagues to free agency. You need a lot so try to move as many as you can. You can do this by trading all the top players from free agency that are not part of your chosen 50 to these other low-level teams to circumvent their minimum 18 skater requirement. This also makes it so that Free Agency has 50 superstar players and the rest are crap.

What you need to do next is move the crappy players from free agency to all the NHL teams (apart from the All-Star teams) to max out each roster and limit them from having room to add new contracts. If you can, max out their goalies too, each team is allowed to have 5. This whole process will take you a little while, but if you want to avoid simming 40+ times like some of the other people in the solutions here have, then it's totally worth it.

Once that's done, go and start up franchise mode with a 32nd franchise with custom rosters. The name, jerseys, etc don't matter.

(VERY IMPORTANT) Edit the settings so that all contracts are extended by 1 extra year to start, no salary cap, easy trade difficulty, the game difficulty is set to rookie, periods are set to 3 mins, injuries are off, the playoffs are single knockout, and whatever other settings there are to make it so that you have minimal involvement and you can sim quicker.

Once it starts up, you'll have to go through the expansion draft. Select the best player possible from each team/players with the highest trade value possible (don't forget about the goalies) and then go to the draft.

When you get to the rookie draft, you can either do as I did and trade your best players/picks to get as many of the top 5 picks as you can to ensure that teams won't get an 80+ player from the draft that they will be able to add to their team instantly & also to fill in the gaps in their rosters or just skip the draft and go to contract resigning (you can also get rid of your players and fill up their rosters later).

Now since you made it so that every player has an extra year added to their contracts, you won't have any contracts to re-sign (not that we would want to re-sign any of our current players anyways) so you can skip ahead to the free agency stage.

(VERY IMPORTANT) Before you sign any players, you want to go into trades and start trading away all your players to other teams. Try to trade to teams with smaller amounts of contracts signed already so that there aren't any teams with less than at least 40 contracts signed. Make sure you're trading your players away for draft picks. You should have 0 contracts by the end of this.

Now you can go into Free Agency and start offering contracts to your chosen 50. Offer every player 1 Mil more than their asking price and keep everything else the same. Sim day by day until you get notifications saying they signed with you. All of them should choose to sign with you, but there might be one or two players that choose to go with a different team for whatever reason, but that's not an issue.

(VERY IMPORTANT) Now, go into your coaching staff screen and fire your head coach. Then, promote your worst rated coach to head coach (mine was the AHL goalie coach who had a rating of D-). Don't worry about filling that coach's position with someone else.

If you haven't already gotten the CHL Scout achievement, you can get it now by going to your scout staff and pressing Y on any scout and changing their region to North America > CHL > WHL, OHL, or QMJHL (you have to change it to one they're not already in). That achievement should pop now.

Now sim to the start of the season. Don't worry about lines or anything, you should have all the top players in the league so it doesn't really matter who plays where. Let the AI decide your lines. Start simming the season. If you did everything right up to this point, your team should have a winning record.

You will get popups, especially at the beginning of the season, from players complaining about their ice-time (which is totally fair when you have 90 OVR players playing on the 4th line and in the AHL lol). Always try to pick the conversation options that limit their morale loss, but don't make any promises about increasing ice time. Pick persuade and tell them it's a team game (or whatever that option actually says) and 7 times out of 10, they will back down.

Keep simming. Later you will start to get popups from players apologizing for their bad performance (I don't get why this is a thing, but whatever). Again, try to limit the amount of morale they lose, but don't make any promises to them.

Keep simming. Throughout the season, you will get popups telling you that other teams have fired their coach. Ignore these for now. Your franchise will also be losing a lot of money, but that won't matter. Neither does repairing/upgrading your arena's facilities either so just ignore all that.

Keep simming. If you handled the players' popups well, you shouldn't run into any morale issues, but there is a chance a player might be too unhappy and request to be traded. Whether or not you trade him is up to you, but I chose to trade him for the top player in the league on another team to avoid any negative repercussions from that player down the road.

Once you get to the playoffs, do not sim any of the games. Make sure you play each one. Since you already set the difficulty to rookie, you can either just play each game to the end or if you want to save time, score a bunch of quick goals so your team has a huge lead (my threshold was 10 goals, but 5 should probably be fine too, 10 is just safer) and then quit. This will sim the rest of the game and if you had a good lead when you do this, there is no chance the other team will catch up to you.

Do this for the Stanley Cup Final game as well and once that game is over, the Cup Champs achievement should pop.

Sim a couple more days and the Coaching Royalty achievement for winning the Jack Adams trophy should pop as well since your D- rated coach took your team to the finals and won the cup in your franchise's first season. At least that's what I assume the game looks at for that trophy got your team into the playoffs. This is what the game seems to look at for this trophy. (Thanks BradLeafsFan9 for this info!)

Now sim through the draft and contract re-signing and get to the free agency stage. Once you're at that stage, go to your coaching staff and fire your head coach. Then click on hire new coach and there should be an A+ coach available for hire. If you don't have the budget for him, fire some more of your coaches to make room. Once you have enough budget to pay for his asking price, send him an offer and sim a couple more days. Once he accepts your offer, the You're Hired achievement should pop. If there is no A+ coach available, you may have to try Emerald Axer's solution in that achievement page.

Hope this helps you guys!