This paper presents new laboratory experiments of two-degree-of-freedom vortex-induced vibration of a flexibly mounted vertical circular cylinder in regular waves. A new experimental model has been developed and tested in the Wind, Wave & Current Tank at Newcastle University. The system mass ratio is close to 3 and the cylinder aspect ratio based on its submerged length is close to 27. The Stokes first-order wave theory is considered to describe the depth-dependent, horizontal velocity amplitude of the wave flow in the circulating water tank. This wave theory is satisfactorily validated by the wave probe measurement. The effects of cylinder stiffness affecting system natural frequencies are also investigated by using a combination of different spring setups in in-line and cross-flow directions. For each set of springs, VIV tests are performed in regular waves, with flow frequency ranging from 0.4 to 1 Hz and amplitude from 0.01 to 0.09 m. The associated Reynolds number at the water surface is in a range of 1.7 × 103–1.5 × 104. The surface Keulegan-Carpenter number (KC) is in the range of 2 < KC < 28 while the surface reduced velocity (Vr) is in the range of 0.5 < Vr < 16 depending on the implemented spring stiffness. Combined in-line/cross-flow oscillations of the cylinder are measured using two non-intrusive Qualisys cameras and the associated data acquisition system. The spring forces are also acquired using four load cells. Results reveal that, depending on KC and Vr, the cylinder primarily oscillates at the flow frequency in the in-line direction and at an integer (mainly 2, 3 and 4) multiple of the flow frequency in the cross-flow direction. Such occurrence of multi frequencies corroborates other experimental and numerical results in the literature. Several peculiar trajectories are observed, including infinity, butterfly, S and V shapes. The present experimental data of vibration amplitudes and oscillation frequencies in in-line/cross-flow directions as well as response patterns provide new results and improved understanding of VIV in oscillatory flows. These will be useful for the development of an industrial tool in predicting offshore structural responses in waves.