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He was forecast, with Daniel Willems, to be the successor to Eddy Merckx. De Wolf seemed to fulfill that promise by having an absolutely dominant 1979 Vuelta a España winning 5 stages including an individual time trial as well as the Points Classification, securing a top 10 place in the General Classification and then following it up by winning the 1980 Giro di Lombardia and the 1981 Milan–San Remo, the last and first classic of the season. He almost won the 1982 Liège–Bastogne–Liège, but he finally lost it to the Italian Silvano Contini in the final sprint due to a shifting error.
After winning a stage in the 1984 Tour de France, his career faded, however the stage win he claimed was an impressive individual effort in which he was able to beat the group of favorites including Bernard Hinault and eventual winner Laurent Fignon by a stunning margin of almost eighteen minutes.
He helped his teammate Eddy Planckaert win the green jersey in the 1988 Tour de France. He ended his career in 1990.
He now helps his wife in her funeral parlour in Dworp, in the south of Brussels.
Although he won the Omloop Het Volk two times, De Wolf was an atypical Flemish cyclist, preferring Italian races such as Milan–San Remo to Paris–Roubaix, Gent–Wevelgem and the Tour of Flanders. He was at ease in hilly races, though he was not an impressive climber.
He complained that he was seen as a 'new Eddy Merckx', that the public had expected too much.