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To start off,

 
you’ll have to launch tf2 and open the dev console. 
 
If you don’t know how to do that, go to the settings in the main menu (gear icon WITHOUT the plus), go to keyboard, find ‘Advanced’ in the keyboard options, and ‘Enable developer console.’ 
 
Press the ` or ~ key to open the console. Type into it just as so: “map pass_brickyard” of course without the quotation marks. Choose a team, and continue to the next section. 
 
 

What to do now

 
Now you should be on the PASS time map brickyard. This is probably the shortest map, and will allow you to rinse repeat as much as possible. Just take the JACK, and take it to the goal. Simple as that. Go Scout for maximum speed and to get this over with fast. After scoring 5 times, you will win the match. Do that 10 times and you’ll get the achievement and hat. 
 
Things to note: 
After a win, the achievement will track 1, and then after another win go to 2. After that, the achievement will go in increments of two. So don’t be afraid it’s you’re on your 3rd win and it says 2/10! Win again and it’ll jump to 4/10 and so on. 
Proof that it works: 
 
 
Questions? Ask in comments! All of them will be answered here: 
 

I hope you enjoy the Guide we share about Team Fortress 2 – How to get the ‘Jackpot!’ Achievement; if you think we forget to add or we should add more information, please let us know via commenting below! See you soon!