We describe combined experiments and simulations of droplet breakup during flow-driven interactions with a circular obstacle in a quasi-two-dimensional microfluidic chamber. Due to a lack of in-plane confinement, the droplets can also slip past the obstacle without breaking. Droplets are more likely to break when they have a higher flow velocity, larger size (relative to the obstacle radius R), smaller surface tension, and for head-on collisions with the obstacle. We also observe that droplet-obstacle collisions are more likely to result in breakup when the height of the sample chamber is increased. We define a nondimensional breakup number Bk ~ Ca, where Ca is the Capillary number, that accounts for changes in the likelihood of droplet break up with variations in these parameters. As Bk increases, we find in both experiments and discrete element method (DEM) simulations of the deformable particle model that the behavior changes from droplets never breaking (Bk << 1) to always breaking for Bk >> 1, with a rapid change in the probability of droplet breakup near Bk = 1. We also find that Bk ~ S^{4/3}, where S characterizes the symmetry of the collision, which implies that the minimum symmetry required for breakup is controlled by a characteristic distance h ~ R.