This study addresses the presence and location of oral lesions in 342 dressage, show jumping, and eventing horses examined at an obligatory veterinary inspection before competing in the Danish National Championship in 2020. Ulcers in the lip commissures were photographed for subsequent pathological analysis. If a lesion was found at the lip commissures on one side, there was an increased risk of finding a similar lesion on the other side (ulcer: p < 0.0001; scar-ring/depigmentation: p < 0.0001; fissure: p = 0.002; erosion/contusion: p < 0.0001). At the lip commissures, external (cutaneous) ulcers were correlated with internal (mucosal) ulcers (p < 0.0001) and with scarring/depigmentation (p < 0.0001). Both mucosal and cutaneous ulcers were correlated with scarring/depigmentation (p < 0.0001). Erosion/contusion at the lip commissures was associated with similar lesions on the bars (p = 0.0002), and ulcers of the buccal mucosa were associated with ulcers on the bars (p = 0.003). Dental hooks or sharp enamel points on one side were associated with similar lesions on the other side (p < 0.0001). Dental findings were not related to mucosal ulcers or erosion/contusion at the lip commissures but were associated with scarring/depigmentation (p = 0.01).