In this paper we investigate the efficiency of using temporal and spatial hardening techniques in flip-flop design for single event upset (SEU) mitigation at different supply voltages. We present three novel SEU tolerant flip-flop topologies intended for low supply voltage operation. The most SEU tolerant flip-flop among the proposed flip-flop topologies shows ability of achieving maximum SEU cross-section below $1.9 \cdot 10^{-10}~\hbox{cm}^{2} /\hbox{bit}$ (no SEUs detected) at 500 mV supply voltage, $4 \cdot 10^{-10}~\hbox{cm}^{2} /\hbox{bit}$ at 250 mV supply voltage, and $2 \cdot 10^{- 9}~\hbox{cm}^{2} /\hbox{bit}$ at 180 mV supply voltage. When scaling the supply voltage from 1 V down to 500 mV, 250 mV and 180 mV, the proposed flip-flops achieve at least $ - 72\% $ , $ - 92.5\% $ and $ - 95\% $ (respectively) reduction in energy per transition compared to a Dual Interlocked Storage Cell based flip-flop when operated at a supply voltage of 1 V. The flip-flops have been designed and fabricated in a low-power commercial 90-nm bulk CMOS process and were tested using heavy ions with LET between $8.6 ~\hbox{MeV-cm}^{2} /\hbox{mg}$ and $53.7 ~\hbox{MeV-cm}^{2} /\hbox{mg}$ .