This letter investigates the effects of the underfill on the wideband flip-chip packaging for 5G millimeter-wave (mm-Wave) applications. For accurate interconnect design, a new hybrid equivalent circuit model is proposed. Targeting at the phased array systems with high density I/Os, a compact anti-pad structure is implemented and co-designed with the high impedance transmission line and the low-cost 90 μm solder balls, compensating the flip-chip capacitive parasitics and realizing the compact low-loss interconnect. To evaluate the underfill effect on the interconnect parasitics, both theoretical analyses and simulations are undertaken. For demonstration, by using a glass substrate with the fan-out process, back-toback flip-chip packaging structures are designed, fabricated, and measured. Measured results demonstrate that with and without underfill U8410-99 the interconnect return loss is better than 20 and 10 dB from DC to 90 GHz, with an insertion loss of 0.2 and 0.45dB at 60GHz, respectively.