This study addresses the description, use-wear analysis, and date of three plate-formed cheekpieces from kurgan 5 at Novoilyinovskiy II, Kazakhstan. They were found in the same context with two sacrificed horses (a stallion and a mare), placed on the bottom of a ritual pit in the “flying gallop” posture. The emergence of horse riding, marking a new type of mobility and warfare, has been traditionally dated to ca 900 BC. However, cheekpieces suggest that this process spanned the entire 2nd millennium BC. They testify to the evolution of horsemanship and the search for the most efficient means of controlling draft and riding horses. Results of the use-wear analysis suggest that all three specimens likely belonged to riding horses’ harnesses. Two AMS radiocarbon measurements referring to kurgan 5 suggest that these cheekpieces are among the earliest used for controlling riding rather than draft horses, implying that horse riding emerged on the Eurasian steppes as early as the beginning of the 2nd millennium BC.