USDF Connection’s inaugural issue was published in May 1999. The May/June 2019 issue celebrated 20 years of publication.
USDF Connection has won more than 30 American Horse Publications Equine Media Awards, including the 2016 award for general excellence.
Before the creation of USDF Connection, USDF members received the quarterly newsletter called USDF Bulletin.
In December 2001, the newly redesigned USDF Connection featured a cover montage of the American flag and a dressage rider, future US Olympian Tina Konyot, as the first issued produced following the 9/11 tragedy.
Still in its infancy, USDF Connection shone an early spotlight on para-dressage, with a September 2003 cover story. A related feature in the issue profiled a then-teenaged Rebecca Hart, who has gone on to become the most decorated US para-dressage competitor in history and, in 2018, became the first US para-dressage athlete to win a World Equestrian Games medal.