We couldn't be well-satisfied taking the black box system results when having in mind that no computer system is free of bugs and that its various aspects related to symbolic integration may seem not quite perfect (see e.g. this remarks). And so our purpose is to calculate this integral with more laborious approach, at least with a few steps which could be checked with a pencil at hand. Nevertheless the system will tackle the problem clearly in a few times more efficient way.
The integrand appears to be quite symmetric and it is convenient to change variables and define a new function. We can see that
f1111[x + w, -x + w, y + z, -y + z] // Simplify
-((x^4 + 6 x^2 y^2 - 3 y^4)/(16 π (x^2 + y^2)^3))
and so we define new variables $$(x_1,x_{11}, x_2, x_{22}) \mapsto (x,w,y,z)=(\frac{x_1+x_{11}}{2}, \frac{x_1-x_{11}}{2}, \frac{x_2+x_{22}}{2},\frac{x_2-x_{22}}{2})$$ and
f[x_, y_] := -((x^4 + 6 x^2 y^2 - 3 y^4)/(16 π (x^2 + y^2)^3))
we calculate the jacobian of this linear transformation
Det @ D[{ x + w, w - x, y + z, z - y}, {{x, w, y, z}}]
4
The function f doesn't depend on w and z and so integration simplifies, however one has to calculate the integration region appropriately. We will integrate the function in two steps, first integrating f with respect x and w (the result will be stored in if) and then if with respect to y and z. Now we find appropriate ranges of variables.
x1x11 = {{-1/2, -1/4}, {-1/4, -1/4}, {-1/4, 0}, {-1/2, 0}, {-1/2, -1/4}}; x2x22 = {{-1/2, -1/2}, {-1/4, -1/2}, {-(1/4), -(1/4)}, {-1/2, -(1/4)}, {-1/2, -1/2}}; tsf = {(#1 - #2)/2, (#1 + #2)/2} &;
now we have
xw = tsf @@@ x1x11 yz = tsf @@@ x2x22
{{-(1/8), -(3/8)}, {0, -(1/4)}, {-(1/8), -(1/8)}, {-(1/4), -(1/4)}, {-(1/8), -(3/8)}} {{0, -(1/2)}, {1/8, -(3/8)}, {0, -(1/4)}, {-(1/8), -(3/8)}, {0, -(1/2)}}
GraphicsRow[{Graphics[{Magenta, Thickness[0.025], Line[x1x11]}], Graphics[{Blue, Thickness[0.025], Line[xw]}]}]

This picture for x1x11 and xw is helpful for appropriate specifications of integration regions. Quite analogical is the region for x2x22 and yz. Integration has to be divided in two subsets for the both regions xw and yz, and so (a simple exercise is left for the reader why integration over w has been changed into multiplication by (2 x + 1/2) for -(1/4)< x <-(1/8)) and (-2 x) for -(1/8) < x < 0, as well as by (2 y + 1/4) for -1/8 < y < 0 and -2 y + 1/4 for 0 < y < 1/8)
and finally we evaluate:
AbsoluteTiming[ if[y_] = Assuming[{-(1/8) < y < 1/8}, 4 (Integrate[f[x, y] (2 x + 1/2), {x, -(1/4), -(1/8)}] + Integrate[f[x, y] (-2 x), {x, -(1/8), 0}])]; int = Simplify[ Integrate[if[y] (2 y + 1/4), {y, -1/8, 0}] + Integrate[if[y] (-2 y + 1/4), {y, 0, 1/8}]]]
{11.3938, (-4π + 8 ArcCot[2] + 8 ArcTan[1/2] + 28 Log[2] - 11 Log[5])/(128 π )}
This timing is for my old and slow laptop (i3, 1.9GHz, 4 GB RAM )
N[int, 20]
-0.0085637914008856298463
Another way is exploiting appropriately ImplicitRegion, however we have performed this way because the transformation tsf is frequently used in physics e.g. retarded and advanced variables.
Timing[Integrate[f1111[x1,x11,x2,x22],{x1,-1/2,-1/4},{x11,-1/4,0},{x2,-1/2,-1/4},{x22,-1/2,-1/4}]]returns{67.340763, (-11*Log[5]+4*(Pi-4*ArcTan[2]+Log[128]))/ (128*Pi)}with no warnings or errors and which should be exactly correct. That number is approximately -0.0085637914008856298463472158822972 $\endgroup$