The quickest method is to start a new "Career", select "Manager Career" and pick either Chelsea or Arsenal (as both teams play in the early season "Community Shield").
From the FIFA 16 "Main Menu" use
to highlight the "Play" tab.
Highlight the "New Career" tile (using
). This tile might say "Load Career" or "Continue Career" - if it does, highlight the tile then use the
to change it to "New Career". Press the
button to begin a new career.
Highlight and select "Manager Career" from the "New Career" menu.
Pick Chelsea or Arsenal as your team (either one will work, as they both play in the Community Shield in early August).
Highlight "Advance" and press the
button to continue. Then repeat once more.
to highlight the "Season" tab.
Highlight the "Calendar" tile (it should already be highlighted, but if not, it's the tile on the top left).
button to select the Calendar.
to switch the Calendar to "August 2015". Use
to move to the date that displays a trophy icon & either Chelsea's or Arsenal's badge (it was August 9 when I completed this).
Now press the
button to sim to this date.
to go back. IMPORTANT:
button and save
you sim the match.
to switch to the "Central" tab. Highlight the "Sim Match" tile & sim the match.
If you win, the achievement pops. If you don't win, then back out, reload your save, and try again until you do win. I got it first try - so I imagine it won't take more than a couple of tries even if you are super, super unlucky.
Alternatively, you can grab these achievements during the process if you are of a mind:
and haven't already popped them. If you do then just sim normally and follow the guides linked above if you are having any issues.