When Does "The Matrix Comics: Sweating the Small Stuff" (1999) Take Place?
"Sweating the Small Stuff" is a science fiction comic-book short written by Bill Sienkiewicz with Spencer Lamm that released April 1st, 1999. So when is "Sweating the Small Stuff" set?
It takes place on the fictional The Matrix timeline roughly in the years:
We know this because at one point Dez sees the digital code behind the virtual reality of the Matrix so it must be after the events seen in the animated short film "The Animatrix: The Second Renaissance" Part II (2003), which takes place between ~2090 AD and ~2199 AD, and the events of the feature film "The Matrix Revolutions" (2003), which takes place in ~2700 AD.

~YEAR AD
We know this because at one point Dez sees the digital code behind the virtual reality of the Matrix so it must be after the events seen in the animated short film "The Animatrix: The Second Renaissance" Part II (2003), which takes place between ~2090 AD and ~2199 AD, and the events of the feature film "The Matrix Revolutions" (2003), which takes place in ~2700 AD.
All that can be said with certainly is that it takes place between 2199 AD and 2699 AD. It is otherwise unplaceable.
The timeline of the Matrix Universe is fairly unique among the largest franchises because the human characters within its fictional world (diegesis) do not themselves know what year it truly is for the duration of most of the stories.
It is a chronologically midway comic short in The Matrix Universe timeline. It can be read at its timeline point.

