Winckelmans played as a midfielder or outside right at the start of the professional era of Olympique Lillois. He participated in the final of the first French Championship on 14 May 1933 at Colombes (O. Lillois-AS Cannes, 4-3). He scored two goals for the nordistes including the winner in the 86th minute.
Winckelmans returned to Olympique lillois in 1937 where he finished his playing career with the start of the war which stopped all club activities. OL merged in 1941 with their neighbour Iris Club Lillois to form OIC Lille. Winckelmans became coach of this new club, until 1943.