Chester-le-Street were relegated back to Division Two at the end of the 1988–89 season, but returned to Division One after finishing third in Division Two in 1991–92. Another relegation in 1996–97 was followed by winning the Division Two title, making an immediate return to Division One. They were relegated again at the end of the 2009–10. After finishing third in Division Two in 2015–16 the club were promoted back to Division One. However, they were relegated back to Division Two at the end of the following season after finishing second-from-bottom in Division One. In 2017–18 the club won the league's Ernest Armstrong Cup, beating Ryton & Crawcrook Albion 2–0 in the final.