Oakes moved to
Third Division side
Chester in the summer of 1976, who had to pay Manchester City a £15,000 fee for his services. Although he initially signed just as a player, he was soon in charge of team affairs at
Sealand Road after manager
Ken Roberts moved upstairs. Oakes was to be
player-manager throughout his six years with the club, where he continued to break playing appearance records. In
his first season at the club, Oakes led Chester to the last-16 of the
FA Cup for the first time since
1891. He would repeat the feat three years later and lead the club to the
Debenhams Cup title in 1977. In
1977–78, he came within a whisker of taking the "Seals" into the top two divisions for the first time, as they finished just two points and places outside the three promotion places. Oakes also gave the legendary
Ian Rush his big break in the professional game, handing him his Chester debut in April 1979. Oakes was widely regarded as having done a good job at Chester, but the
1981–82 season saw the "Blues"
relegated. Oakes left the club in March 1982 and never again managed in the Football League. ==Coaching career==