Wintering played four seasons of college basketball with the Portland Pilots.[2] He averaged 14.1 points and 5.2 assists in 110 games with the Pilots.
As a freshman in the 2013–14 season, Wintering was the Pilots' starting point guard for the first 27 games of the season before suffering a leg injury.[3]
Wintering returned to the starting lineup for the Pilots as a sophomore in 2014–15 and set the Pilots' single-season record for assists with 187. His 45.8% three point shooting ranked fifth best in a season in Pilots' history. For his performances over the season, Wintering was named second team all-West Coast Conference.[3]
As a junior in 2015–16 Wintering again improved his production. He scored 18.3 points per game and led the team in points, assists and steals. His 584 points scored ranked second all-time at Portland in a single season. Wintering was named first team all-WCC at season's end.[3]
A repeat performance was expected from Wintering as a senior, and he was named preseason first team all-WCC. He lived up to the billing, scoring 19.5 points and dishing out 5.6 assists per game before a mid-January knee injury sidelined him for the rest of the season. Wintering's final career game for Portland came on January 19, 2017 at San Francisco, when he tore his ACL.[4] Despite missing nearly two months to end the season, Wintering was named honorable mention all-WCC as a senior.[5]
Professional career
Araberri (2017–2018)
In September 2017, Wintering signed a one-year contract with Araberri BC of the Spanish LEB Oro.[6]
Dutch Windmills (2018–2019)
On August 1, 2018, Wintering was announced by Dutch Windmills of the Dutch Basketball League (DBL).[7] In October 21, he suffered an injury which included a broken fibula. In January, he returned to the starting line up.[8] On 10 April 2019, Windmills withdrew from the DBL due to its financial problems.[9]