He started playing football for the youth team of HFC Haarlem, but stopped at age 18 in 1987 to become head of the youth team. After a brief venture as a player and administrator, Raiola remained involved in the football world, this time as a football agent. He began working at Sports Promotions, a sports agent company, and assisted in the transfers of several high-profile Dutch players to Italian clubs, including Ajax player Bryan Roy (in 1992 to Foggia), Marciano Vink (in 1993 to Genoa), Wim Jonk and Dennis Bergkamp (both in 1993 to Internazionale) and Michel Kreek (in 1994 to Padua). After a while, however, he decided to leave the company and start his own business. His first independent big transfer was Pavel Nedvěd's signing from Sparta Prague for Lazio following his impressive performance at UEFA Euro 1996, where Nedvěd's Czech Republic reached the final.