Equine Gastric Ulcers Syndrome (EGUS) is a worldwide disease present in equids of different breeds, activity levels, and age groups. It is divided into two different illnesses: Equine Squamous Gastric Disease (ESGD) affecting the squamous mucosa and Equine Glandular Gastric Disease (EGGD) affecting the glandular mucosa. The historical horserace is a traditional competition that is common in Italy. They can be divided into two different types: speed races and jousting tournaments. Anglo-Arabians and Thoroughbreds are used for the two competitions with training and management systems similar to those used in races performed on a racetrack. The aim of this study was to determine the prevalence of ESGD and EGGD in horses used for historical horseracing and evaluate the differences in the presence of the diseases in animals of the two different breeds used for the two types of competition. A cohort of 73 horses was enrolled in this study, which were stabled in 10 training facilities and performed two jousting tournaments and one speed race. An ESGD at least of grade 2 was found in 88% of horses with all degrees of severity seen; EGGD was diagnosed in 45% of animals. In this cohort of horses, the presence and severity of ESGD and EGGD are similar to that in reports in racehorses performing on racetracks. Anglo-Arabians used for speed races are more affected by ESGD and EGGD, which is probably because they are involved in a higher number of races and travel more during the year compared to Thoroughbreds used for jousting competitions.