Richard Day is a commercial breeder and currently races a few of his homebreds under the guidance of his trainer and sister, Catherine Day Phillips. Peggy O a four year-old filly is a winner of five of her nine career starts,with earnings of more than $180,000 and winner Aunt Sue (in partnership with Tracey McCowen) and maiden Rainbows Ahead.
Richard Day is the breeder of 2016 Woodbine Oaks winner Neshama (Sligo Bay (IRE) – Catch A Fire, by Indian Groom) $413,200 in career earnings; as well as 2008 2 Year-old Filly Champion and Graded Stakes winner, Van Lear Rose (Stroll – Devaluation, by Conquistador Cielo) and 2001 Champion Turf Mare and Multiple Graded Stakes winner, Sweetest Thing (Candy Stripes – Escape Reality, by Lear Fan). Escape Reality is the granddam of Neshama. All, except Sweetest Thing, who was sold at auction to Stud TNT , were trained by Catherine Day Phillips.