In addition to the individual and single-boat awards given at the Regatta, 2009 will mark the second year of the Leukemia Cup Challenge.  In the Challenge, three-boat teams will use their sailing and fundraising abilities to compete for the prestigious Challenge trophy, which will be awarded at the Regatta's closing ceremony. 

The Challenge trophy is a perpetual trophy.  The winning team will choose where it will be displayed until the following year's Regatta, when it will be passed to the next year's winning team.  The Challenge trophy will include a permanent engraved plate listing the name of the winning team, the yacht club which it represents (if any), and the year of the competition. 

Sailors wishing to compete in the Leukemia Cup Challenge will form a team comprised of three boats, all of which must be registered in The Leukemia Cup Regatta.  Skippers who wish to participate in the Challenge, but who are unable to field a full three-boat team, may enter a lottery for random team assignment.  A yacht club may field more than one team; teams representing a yacht club may be comprised of yachts from outside the club, as long as one of the three is a member of said club.  Teams may be comprised of boats from the same racing class or multiple classes. 

Scoring for the Challenge will include the combined sailing and fundraising scores of each of the team's boats.  Individual boat scores are the sum of the race points earned within each class for the five races, plus the overall fundraising ranking score of the boats.  Challenge team score ties will be resolved based on the team totals of race placement. 

The Challenge trophy stands over two feet tall and features a nickel-plated, tarnish-free cup attached to a solid walnut base with chrome engraved plates.  Generously donated to The Leukemia Cup Regatta by Dr. Jack and Karen Drogt of White Bear Lake, the Challenge trophy honors the memory of Karen's father, William "Bill" Sandberg.  Sandberg, longtime mayor of North St. Paul, lost his battle with leukemia in April 2008.