1938/39: After playing as a Midwestern amateur barnstorming team, the Sheboygan Red Skins joined the industrial National Basketball League. The Red Skins were coached by Edwin “Doc” Schutte, a local dentist. The Red Skins would post a record of 11-17 and finished third in the Western Division in their first season in the NBL.

1939/40: Doc Schutte would step down as coach and was replaced by Frank Zummach, who began to mold the Red Skins into a contender. The Red Skins would reach the playoffs with a record of 15-13 and faced the Oshkosh All-Stars in a three-game series for the Western Division championship, losing a hard-fought three-game series.

1940/41: The Sheboygan Red Skins continued to improve in their third season, finishing 13-11 for the second-best record in the NBL. The Red Skins would reach the NBL Finals by edging the Detroit Eagles in a three-game series. However, the NBL Finals would end in disappointment for Sheboygan, as they lost two straight against the Oshkosh All-Stars.

1941/42: The Sheboygan Red Skins suffered a letdown season, missing the playoffs as they posted a record of 10-14.

1942/43: A new arena opens for the Sheboygan Red Skins, who hired Carl Roth to replace Frank Zummach as their head coach. The 3,500 Sheboygan Municipal Auditorium and Armory was built as part of a public works project and was the envy of the NBL. The Red Skins would get a big boost with the acquisition of Buddy Jeannette. Jeannette worked at a defense plant in Rochester and played in the NBL on weekends. Buddy Jeannette averaged 15.6 points per game and helped the Red Skins finish 12-11 and capture second in the NBL standings. In the playoffs, the Red Skins finally solved the Oshkosh All-Stars to reach the NBL Finals, where Sheboygan led by the play of Buddy Jeannette the Red Skins won a three-game series against the Fort Wayne Zollner Pistons to claim their first National Basketball League Championship. Other significant contributors to the Red Skins’ first championship team were NBL rookie of the year Ken Buehler, and all-league players Ed Dancker and Kenny Suesens.

1943/44: Coming off a championship, the Red Skins remained one of the strongest teams in the NBL, finishing the season in second place with a record of 14-8. Leading the way were players like Mike Novak. The Red Skins would reach the NBL Finals again, beating the Oshkosh All-Stars in a three-game battle. However, in a rematch against the Fort Wayne Zollner Pistons, the Red Skins quest for a second straight title would come up short as they lost three straight.

1944/45: The Sheboygan Red Skins coached by Dutch Denert remained one of the strongest teams in the NBL, winning the Western Division Championship with a record of 19-11. The Red Skins would once again reach the finals by beating the Chicago American Gears in a three-game series. For the third straight season, the Red Skins would face the Fort Wayne Zollner Pistons in the NBL Finals. Things looked good early as they won the first two games in the best of five series. However, the Pistons would win the next three games and repeat as champions of the National Basketball League.

1945/46: Once again, the Sheboygan Red Skins would capture the Western Division Championship, posting a record of 21-13. The Sheboygan Red Skins would defeat the Oshkosh All-Stars in a hard-fought five-game series to reach the NBL Finals for the fourth straight season. Facing a solid Rochester Royals team, the Red Skins started strong winning the first two games in the best of five series. However, once again they would drop the next three games and lost the series in five games.

1946/47: With the end of World War II, professional basketball finally had room to grow. The NBL was still primarily an industrial league its tenth season, as major East Coast arena owners, were creating their league called the Basketball Association of America. The Sheboygan Red Skins started the season in Los Angeles, playing a series of games against western teams, the first NBL team to play on the West Coast. One game against the Los Angeles Red Devils saw them face Jackie Robinson months before he would break baseball’s color barrier. The Red Skins would finish the season with a record of 26-18, missing the division title by two games. In the playoffs, the Red Skins would lose a hard-fought five-game series to the Oshkosh All-Stars in the opening round of the NBL Playoffs.

1947/48: It would be a chaotic season for the Sheboygan Red Skins as Bobby McDermott was acquired from the Chicago American Gears to be the team’s player-coach. However, after just a month in Sheboygan, McDermott left to play with the Tri-Cities Blackhawks. Aging and dealing with injuries, the Red Skins would finish in last place with a disappointing record of 23-37.

1948/49: The Sheboygan Red Skins rebuilt their team with youth, signing players like Kentucky all-American Bob Brannum, Milt Schoon of Valparaiso, Texas Guard Danny Wagner, Guard Merlin “Boody” Gilbertson from Washington, Iowa Center Noble Jorgensen and local favorite Bobby Cook from Wisconsin. The Red Skins would rebound nicely, posting a record of 35-29. However, in the playoffs, the Red Skins would make a quick exit with two straight losses to the Tri-Cities Blackhawks. It would mark the final year of the NBL as the league merged with the Basketball Association of America. The Sheboygan Red Skins were one of the NBL’s most successful franchises, only the Oshkosh All-Stars, with six, appeared in more NBL Championship Series and played more seasons in the NBL than the Red Skins.

1949/50: The Sheboygan Red Skins were one of seven NBL teams to join the BAA as the two leagues merged to become the National Basketball Association. The Red Skins, despite their success, were doomed from the start, as they had the smallest arena and smallest market in the NBA. The Oshkosh All-Stars folded, allowing the Red Skins to lay claim to the oldest team in the NBA. Coached by Ken Suesens, the Red Skins lost to fellow NBL alum Rochester Royals 108-75 in their first NBA game on November 1st. The Red Skins would rebound to win their next six games, but could not maintain any form of consistency as they lost nine straight soon after. Often the Red Skins played well at home, posting a 17-14 record, including an 85-82 win over the eventual champion Minneapolis Lakers on January 5th in front of a standing-room crowd of 3,800. However, injuries and struggles on the road led Sheboygan to finish the season in fourth place with a record of 22-40. In the playoffs, the Red Skins battled hard but lost a three-game series to the Indianapolis Olympians. A month after the playoffs ended, the Sheboygan Red Skins withdrew from the NBA. They would play one more season in the National Professional Basketball League. However, the NPBL folded before completing its first season, and despite their best efforts to carry on in other leagues and as an independent team, failed to gain any steam as the NBA took roots and became the standard-bearer of Professional Basketball.