A study of the initial state gluon radiation (ISR) measurement in proton-antiproton collisions at $\sqrt{s}$ = 1.96 TeV is presented. This analysis uses Drell-Yan ($Z/\gamma^* \to ee,\mu\mu$) events in the CDF data sample, corresponding to an integrated luminosity of 9.4 $\mathrm{fb^{-1}}$. We find that the mean value of the transverse momentum distribution of the Drell-Yan system ($\langle p_T^{DY} \rangle$) is a good observable to measure the effect of the ISR. This observable has a logarithmic dependence on the mass square of $Z/\gamma^*$ boson ($m^2_{DY}$), which is parameterized as a linear function of $\langle p_T^{DY} \rangle = (-7.57 \pm 0.69) + (2.15 \mp 0.08)\log m^2_{DY}$. This measurement provides a way to estimate the effect of softly evolving ISR at very high mass region, and it can be used to control the ISR effect in other physics processes.