In his capacity as assistant manager to boss Paul Collicutt, 'Boylo' was taking Evesham United's warm-up before their home FA Cup third qualifying round tie against Chalfont St Peter when he suffered a dislocated knee cap.
He was taken to hospital in Redditch where he is now awaiting surgery, which is likely to take place in Banbury.
"I just clipped the ball to someone when my knee came apart and it was extremely painful," Boyland said.
"I had a half-knee replacement around three-and-a-half-years ago and it has basically come apart."
Boyland netted more than 100 goals for the Robins in three separate spells, initially arriving from Banbury United in 1984.
Collicutt, who played alongside Boyland in Cheltenham's 1984/85 Southern League title winning season, said Evesham won their FA Cup tie for Boyland, eventually progressing to the fourth qualifier with a 4-1 win having fallen behind early on.