The Interscholastic Sailing Association (originally known as the Interscholastic Yacht Racing Association, abbreviated as IYRA, now as ISYRA) was founded in 1930 by a group of eastern preparatory school headmasters in order to give schoolboys a chance to develop their yachting interest, just as college men had been doing. Every spring since then, with the exception of the World War II years, member schools have competed for the trophy presented by Clifford D. Mallory.

There have been significant changes in the course of the Association's 50-year history. Girls have entered the ranks of competitors, and high schools have become members. In 1963, the Association became incorporated legally, and subsequently it has qualified as a non-profit, charitable organization. Thus gifts to the Association qualify for tax exemption under federal laws.

In an effort to encourage secondary school sailing throughout the United States, in 1973 the Interscholastic Yacht Racing Association changed its emphasis to become more of a national body overseeing regional associations. At present there are ISYRA member associations in New England, the Middle Atlantic States, the Southwest, Southern California, and Northern California.

Traditionally, the annual Mallory Trophy Regatta has been sailed in larger boats such as Atlantics, USNA Knockabouts, Ravens, Shields, and 210s. However, responding to the popularity of small-boat racing among youthful sailors, since 1973 the regatta has been in 420s, Flying Juniors, and Interclub dinghies. Each ISYRA regional association is entitled to send school teams to the Mallory regatta in New England.

In February 1992 the organization changed its name. It is now known as the Interscholastic Sailing Association (ISSA).