Sailing Professional ~ Brand Ambassador  ~ World Champion

Skip Dieball’s sailing career has evolved from regional champion to world-wide sailing icon, as evidenced by his nomination for the ROLEX YACHTSMAN OF THE YEAR (2004 & 2015), nomination for US SAILINGS Sportsman of the year (2010), US SAILING Champion of Champions (2009) and World Champion (2015, 2022, 2026).

In his sailing career, Dieball has earned over 40 Major One Design Titles (World, Continental, National & Midwinter).  In addition to these achievements, he actively pursued an opportunity to represent the United States in both the 2000 and 2004 Olympic Games.  Dieball has also participated in two Pan-American Games (2011 as Coach and 2019 as Competitor). 

Dieball continues to build on his success on and off the water. Most recently, he’s helped organizations elevate their sailing programs.  Dieball is past Waterfront Director and Assistant General Manager at the Chicago Yacht Club and past Executive Director of Sheridan Shore Sailing School in Wilmette, Illinois.  There, he and his teammates inspired new sailors to learn the beauty of sailing and compete on the race course.  

Born and raised in Toledo, Ohio, Dieball graduated from Eastern Michigan University.  He is a member of the US SAILING, Inter-Lake Yachting Association, North Cape Yacht Club, Four Lakes Ice Yacht Club, Wilmette Harbor Club and various class associations.

Want to reach out to Skip directly?  skip@dieballsailing.com