What year does Bully take place?

[T-Bone]

I had a pinball machine!

[Hayley]

Gotta love pinball. It's a classic.

The calender matches September 2005, and September is usually the month everybody is sent back to school.

I took a look at the calendar in the PS2 version and noticed that the first day started on a Friday. If the academy starts in September like most normal schools, the date would be September 2006.

[Mike_W]

I just noticed, they spelled the word "calendar" wrong in the game!

[Hayley]

And it looks like I fell for the mistake. Oh well.

[BloodChuckZ]

So ?  You expect them to spell it right ?  It's Bullworth Academy !

[Hayley]

This is true.

[BullyFanatic]

Well, The timeline of the game is vastly unclear. Design influences (of cars and architecture) point to a possible setting in the 1980s or 1990s, but there are also other objects hinting at a setting in 2006, 2007 or 2008.

■A reference to the year being 1992-1995 as the setting can be seen in one of the various arcade machine minigames
■School sports flags show the school as champions as recently as 1998-1999.
■On their website they say it is fall 2006.
■A poster can be seen in the Jock Clubhouse that dates to 2005, and another to 2007.
■Mr Galloway alludes to surfing "dubious sites" on the internet. Additionally, two modern computers can be found in the basement bedroom of Dragon's Wing Comics.
■In contrast to the above, the School Library has a couple of vintage, 70s-80's-esque monochrome-screen computers.

source -bully.wikia.com

[Mike_W]

I think it would be safe to say '06-'07. The cars look like they are from the '60s-'80s and the architecture is WAY older than that. Most of the interior and exteriors of the buildings look like they are from 1950 and prior.

[Hayley]

Thanks for that! I meant to go around and take more pictures, but never did. I'm not very far in the PC version anyway.

My thoughts on the arcade games:
 

Here it is.

I think it's 1995 due to the arcade games.

Just because the arcade game says copyright 1995 doesn’t mean that the game takes place in ‘95. There are plenty of people who have arcade games in their house today. Hell, there’s a burger joint around here that has a classic Mrs. Pac-man game in it, and I don‘t think the people that go/work there are teleported back to 1981.

■In contrast to the above, the School Library has a couple of vintage, 70s-80's-esque monochrome-screen computers.

I still believe that the '70s/'80's stuff around Bullworth are to appeal to the older people who play the game, like the pepole who grew up in the 1980's.

■On their website they say it is fall 2006.
■A poster can be seen in the Jock Clubhouse that dates to 2005, and another to 2007.

FALL 2006. By the time you unlock the Jock Clubhouse (and Chapter 4), Christmas (and New Years) will have passed, bringing the game into winter, spring, and (endless) summer '07.

[BloodChuckZ]

^ That last is just my position.  Not gonna have that stuff in there if it ain't happened yet.