Gamma-ray observations have long been used to constrain the properties of dark matter
(DM), with a strong focus on weakly interacting massive particles annihilating through
velocity-independent processes. However, in the absence of clear-cut observational evidence for
the simplest candidates, the interest of the community in more complex DM scenarios involving a
velocity-dependent cross-section has been growing steadily over the past few years. We present
the first systematic study of velocity-dependent DM annihilation (in particular p-wave
annihilation and Sommerfeld enhancement) in a variety of astrophysical objects, not only including
the well-studied Milky Way dwarf satellite galaxies, but nearby dwarf irregular galaxies and local
galaxy clusters as well. Particular attention is given to the interplay between velocity
dependence and DM halo substructure. Uncertainties related to halo mass, phase-space and
substructure modelling are also discussed in this velocity-dependent context. We show that, for
s-wave annihilation, extremely large subhalo boost factors are to be expected, up to 1011
in clusters and up to 106–107 in dwarf galaxies where subhalos are usually assumed not to play
an important role. Boost factors for p-wave annihilation are smaller but can still reach 103
in clusters. The angular extension of the DM signal is also significantly impacted, with e.g. the
cluster typical emission radius increasing by a factor of order 10 in the s-wave case. We also
compute the signal contrast of the objects in our sample with respect to annihilation happening in
the Milky Way halo. Overall, we find that the hierarchy between the brightest considered targets
depends on the specific details of the assumed particle-physics model.