We present a thorough investigation into the efficacy of 19 density functional theory (DFT) functionals, relative to RI-CC2 results, for computing two-photon absorption (2PA) cross sections (σ^2PA) and key dipole moments (|μ₀₀|, |μ₁₁|, |Δμ|, |μ₀₁|) for a series of coumarin dyes in the gas-phase. The functionals include different categories, including local density approximation (LDA), generalized gradient approximation (GGA), hybrid-GGA (H-GGA), range-separated hybrid-GGA (RSH-GGA), meta-GGA (M-GGA), and hybrid M-GGA (HM-GGA), with 14 of them being subjected to analysis for the first time with respect to predicting σ^2PAvalues. Analysis reveals that functionals integrating both short-range (SR) and long-range (LR) corrections, particularly those within the RSH-GGA and HM-GGA classes, outperform the others. Furthermore, the range-separation approach was found more impactful compared to the varying percentages of Hartree–Fock exchange (HF E_x) within different functionals. The functionals traditionally recommended for 2PA do not appear among the top 9 in our study, which is particularly interesting, as these top-performing functionals have not been previously investigated in this context. This list is dominated by M11, QTP variants, ωB97X, ωB97X-V, and M06-2X, surpassing the performance of other functionals, including the commonly used CAM-B3LYP.