José Gregório began his career without great expectations, but evolved consistently until becoming one of the best Portuguese surfers. He first stood out in national finals and on the European EPSA circuit, winning at Ribeira D’Ilhas in 1994. He was national champion in 1997, 2003, and 2007, having fiercely contested titles with João Antunes, in a rivalry that even led to the creation of an alternative circuit (the ANS Tour).

On the international stage, he achieved significant results in the QS, including victory at the Gaia Shopping Buondi Pro in 2001, as well as finals in several European events and solid performances on the EPSA. He managed to compete for a full season on the QS, finishing in 114th place. Among other achievements, he reached the finals of the Billabong Challenge and won an AirShow in England, competing against world-class surfers.

Outside of competition, José Gregório stood out for his strong media presence and for surfing heavy waves in Ericeira, Madeira, and Nazaré, being a pioneer of tow-in surfing in Portugal. After his third national title, he gradually transitioned into the business side, taking on roles at Quiksilver until becoming European Franchise Director at Boardriders.