On January 29, 2009, Winkelsas became the first member inducted into the University of South Carolina Salkehatchie athletic hall of fame. Winkelsas pitched for the USC Salkehatchie Indians from 1993-1995. While still at USC Salkehatchie, he was drafted by the Philadelphia Phillies in 1994 but did not play. From USC Salkehatchie he transferred to Division II Elon College in North Carolina where he led the nation in era with 1.29.
In 1996, Joe signed with the Atlanta Braves and played at every level of that organization. While with the Braves, in 1998 he led the Braves organization in saves with 22. He was among the Braves minor league leaders in era in 1997, 1998 and 2002. Joe was selected to the Maryland fall league All-Star Team in 1998 and led that league in saves. He was also named to the AA Southern League All Star Team in 1999.
Joe Winkelsas made his major league pitching debut on April 10, 1999 with the Atlanta Braves. In 2004, 2005 and 2008, Joe pitched for the White Sox Organization with the AAA Charlotte Knights.
While working as a pitching coach for Division I Niagara University in Buffalo NY in 2006, Joe’s players challenged him to go to local tryouts for the Milwaukee Brewers. He did and was in the top 10 in that league in era, making his second appearance in the major leagues with the Brewers that year.
He retired from baseball in summer of 2008 and now owns and operates a baseball academy in his hometown of Buffalo, New York.