This work reports an experimental study of the turbulent entrainment into the planar wake of a circular cylinder, exposed to various turbulent backgrounds, from the near- to the far-field. The background turbulence features independently varying turbulence intensity and integral length scale, thereby rendering different turbulent/turbulent interfaces (TTIs) between the background and the primary flow (wake). Combined, simultaneous particle image velocimetry and planar laser induced fluorescence measurements were conducted to quantify the entrainment characteristics across these various TTIs at an inlet Reynolds number of 3800. The primary focus was on understanding how turbulent entrainment evolves spatially in conjunction with the rapid development of the large-scale coherent vortices in the planar wake, and how such evolution is affected by the background turbulence. It is found that TTIs can establish two layers when the background turbulence is sufficiently intense, which distinguishes TTIs from the turbulent/non-turbulent interface (TNTI). The two layers are underpinned by different physical mechanisms but have the same thickness and appear to scale with the local Kolmogorov length scale after the wake spreading transition position (Chen & Buxton, J. Fluid Mech., vol. 969, 2023, A4). It is also found that the probability density functions of the entrainment velocity for both TTIs and a TNTI display power law tails, which are associated with extremely large entrainment velocities occurring more frequently than for a Gaussian process. These intermittent, extreme entrainment velocities make a remarkable contribution to the mean entrainment velocity, particularly in the near wake, which leads to a much higher mean entrainment velocity than farther downstream, for both a TNTI and the TTIs. Conditionally averaged analysis reveals that these extreme events of the entrainment velocity are directly associated with intense enstrophy structures close to the interface.