Abstract: A good horse-rider ‘match’ is important in the context of equine welfare. To quantify the influence of repetition and horse-rider matching on the stress of horses encountering challenging objects, 16 Warmblood horses were ridden in a test-setting on three occasions. On each occasion the horse was ridden by a different rider and was challenged by three objects (A–C). Heart rate (HR), heart rate variability (HRV) of horse and rider, and behaviour score (BS) of the horse were obtained for each object and as a total for each test. The horse-rider interaction was evaluated with each combination and assessed as ‘matching’ or ‘mismatching’, and the horses were categorised as ‘compliant’, ‘partly-compliant’ or ‘non-compliant’. Horses exhibited a decreased HR (P = 0.015) and a decreased BS (P = 0.004) within and across different tests. ‘Matching’ horse-rider combinations exhibited less stress as indicated by reduced HR (‘match’ 69 ± 10 vs. ‘mismatch’ 72 ± 9, P = 0.001) and BS (‘match’ 1.9 ± 1.1 vs. ‘mismatch’ 3.8 ± 1.4, P = 0.017) of the horse. ‘Compliant’ (68 ± 8, P < 0.001) and ‘partly-compliant’ (71 ± 9, P = 0.002) horses had significantly lower HR than ‘non-compliant’ (75 ± 9) animals. The findings of the study indicate that HR and BS measurements support a subjective ‘match’ diagnosis and HR measurement may be a valuable tool in assessing horse compliance.