Having made eight appearances for QPR during the first half of the 2018–19 season,[16] Chair joined League Two club Stevenage on a loan deal for the remainder of the season on 31 January 2019.[17][18] He made his Stevenage debut in the club's 1–0 victory over Yeovil Town at Broadhall Way on 2 February 2019, playing the full match.[19] Chair scored his first goals for Stevenage by scoring two long-range efforts late-on in a 2–2 away draw at league leaders Lincoln City on 16 February 2019.[20] A month later, on 12 March 2019, he scored from within his own half in Stevenage's 2–0 home win against Swindon Town.[21] Chair was nominated for League Two Player of the Month for March 2019 having contributed four goals and four assists during the month.[22] He made 16 appearances during the loan agreement, scoring six times and assisting six goals.[16][23] Stevenage manager Dino Maamria described Chair as "the best player that has ever worn the Stevenage shirt", as well as the best player to have ever played in League Two.[23]