A high prevalence of both squamous (ESGD) and glandular (EGGD) ulcers was previously found in, mainly young, Icelandic horses coming into training for the first time. This study evaluated risk factors for gastric ulcers in Icelandic riding horses at various ages and stages of training. The horses (n = 211) were gastroscoped from 21 equine establishments across Iceland. A variety of morphometric, clinical, behavioural and management factors were evaluated as potential risk factors for gastroscopically significant (grade ≥ 2/4: found in 27% of horses) or gastroscopically severe (grade 3 or 4/4: found in ~10% of horses) ESGD or gastroscopically significant EGGD (grade ≥ 1/2: found in 46.4%). Body condition score (BCS), cresty neck score (CNS), stable/turnout behaviour, exercise intensity/frequency and age were not significantly associated with ESGD or EGGD ulcer score. However, having come off the pasture into training for 4 weeks or less was a significant risk factor for gastroscopically significant and severe ESGD compared to 5 weeks or more. For both EGGD and ESGD, “region” was important. Gastroscopically significant EGGD and gastroscopically severe ESGD were more prevalent in those showing clinical signs often associated with ulcers. Geldings were more likely to have gastroscopically significant ESGD than both mares and stallions and more EGGD than stallions. Being stabled, but spending >2 h/day out in the paddock, compared with <2 h paddock time or full-time turnout, was protective for gastroscopically significant ESGD as was being fed complementary feed (all fed <1 g non-structural carbohydrate (NSC)/kg/BW/meal). Being at a training establishment for >4 weeks was protective for gastroscopically significant and gastroscopically severe ESGD but not EGGD. This study confirms the relatively low prevalence of ESGD in Icelandic horses being kept in training establishments and fed low NSC diets but highlights the high prevalence of EGGD.