The shedding sequence of the Loop Current (LC) inside the Gulf of Mexico (GoM) is strongly influenced by cyclonic frontal eddies around its edge. Along-track altimetry data, analyzed based on a wavelet decomposition to provide estimates of individual cyclones’ diameter, amplitude and relative vorticity, and in situ surface drifter data from the Global Drifter Program, are used to investigate the cyclonic activity in the eastern Gulf of Mexico, where the LC extends and retracts. By analyzing this ∼20 year long (1992–2011) combined set of observation data records, we were able to complement previous findings, to confirm results from modeling studies and to provide new insights on the LC frontal dynamics.