We have combined X-ray observations from Chandra with Sunyaev–Zel’dovich effect data from Planck and Bolocam to measure intracluster medium pressure profiles from 0.03 R 500 ≤ R ≤ 5 R 500 for a sample of 21 low-z galaxy clusters with a median redshift of 〈z〉 = 0.08 and a median mass of 〈M 500〉 = 6.1 × 1014 M ⊙ and a sample of 19 mid-z galaxy clusters with 〈z〉 = 0.50 and 〈M 500〉 = 10.6 × 1014 M ⊙. The mean scaled pressure in the low-z sample is lower at small radii and higher at large radii, a trend that is accurately reproduced in similarly selected samples from The Three Hundred simulations. This difference appears to be primarily due to dynamical state at small radii, evolution at intermediate radii, and a combination of evolution and mass dependence at large radii. Furthermore, the overall flattening of the mean scaled pressure profile in the low-z sample compared to the mid-z sample is consistent with expectations due to differences in the mass accretion rate and the fractional impact of feedback mechanisms. In agreement with previous studies, the fractional scatter about the mean scaled pressure profile reaches a minimum of ≃20% near 0.5 R 500. This scatter is consistent between the low-z and mid-z samples at all radii, suggesting it is not strongly impacted by sample selection, and this general behavior is reproduced in The Three Hundred simulations. Finally, analytic functions that approximately describe the mass and redshift trends in mean pressure profile shape are provided.