Flexion of the horse\'s head and neck during dressage riding reduces the pharyngeal lumen with the risk of increased upper airway resistance and upper airway obstructions. According to the Fédération Equestre Internationale, hyperflexion is achieved through force, whereas the position low-deep-round is nonforced. The objectives of this study were to evaluate (1) applied rein tension and (2) dynamic structural disorders in the upper airways in dressage horses in different gaits and different head-neck positions (HNPs). Overground endoscopy (OGE) and rein tension were evaluated in 13 clinically healthy and high-performance Warmblood dressage horses while being ridden in a standardized program comprised of four different gaits (halt, walk, trot, and canter) and in four HNPs (unrestrained, competition frame, hyperflexion, and low-deep-round). All included horses were able to achieve the desired HNPs. The HNP low-deep-round showed significantly lower rein tension than competition frame (P < .001) and hyperflexion (P < .001). An association was found between dynamic structural disorders in the upper airway tract evaluated by OGE and head-neck flexion, but this association was not linked to the degree of flexion. The HNP hyperflexion was neither associated with greater rein tension nor severe dynamic structural disorders than the HNP competition frame. This study confirms that low-deep-round is a nonforced position, in contrast to hyperflexion. Further studies are needed to evaluate whether dynamic structural disorders are a result of flexion or if the degree of flexion has an impact.