The Stamford Denmark Friendship Race was first staged in 1966, as part of a weeklong commercial promotion and cultural exchange called the Stamford Denmark Friendship Week.  The week was initiated by Werner Valeur-Jensen, a Danish resident of Stamford, then Chairman of the Stamford Chamber of Commerce.

That first race had 21 entries that sailed a triangle course off the Stamford breakwater, the winners receiving a case of Danish beer.

As the tradition grew, so did the close relationship between the Stamford Yacht Club and the Royal Danish Yacht Club (KDY).  That relationship continues today, with participation of KDY sailors in the race.  The Stamford Sail and Power Squadron, and the Consulate General of Denmark were also early partners in the event and continue to be involved.

In 1976, Her Majesty Queen Margrethe the Second and His Royal Highness Prince Henrik of Denmark, honored Stamford with a royal visit to participate in the event, the Prince racing as co-captain on Charisma.  Later, in 1982, Prince Henrik returned to race aboard Boomerang, winning the Denmark Cup. In 1986, the Prince accepted honorary citizenship of Stamford and honorary membership to the Stamford Yacht Club, after racing on Nirvana in that year's event.

In 1990, Prince Henrik returned for the Club's Centennial Celebration and the 25th anniversary of the Stamford Denmark Friendship Race. Racing aboard Robert C. Towse, Jr.'s Blue Yankee, he again won the Denmark Cup.

For the 50th Race in 2015, a contingent of KDY sailors led by Commodore Lars Ive and including Olympic Finn Class silver medalist Jonas Høgh-Christensen, participated in the festivities. On the Saturday presiding the Denmark Race they won the Valeur-Jensen Cup in a friendly match race series with SYC raced in Oyster Bay onboard Swedish Match 40s. The following day, they sailed in the Denmark Race onboard the Danish made Xp44 Warrior Won owned by Larchmont Yacht Club member Chris Sheehan. They placed first in their fleet, winning the Tuborg Skål Bowl. Off the water, events celebrating the fifty years of friendship between Stamford and Denmark included a special ballet performance by stars of the Royal Danish Ballet and the New York City Ballet at the Palace Theater, and a chill music festival with Danish DJ group Stella Polaris in Mill River Park.