A midfielder and later defender, Perryman played in a club record 866 first team appearances, in all competitions for Tottenham Hotspur between 1969 and 1986. During his seventeen-year career with the north London club, Perryman collected many medals, winning the UEFA Cup in 1972 and 1984 (playing in both legs of the 1972 final and just the first leg of the 1984 final), the FA Cup in 1981 and 1982 and the League Cup in 1971 and 1973.
Perryman became manager of Watford from 1990–93 saving them from relegation in the early years, before managing Start in Norway (1995),Shimizu S-Pulse, (1996–2000) and Kashiwa Reysol in Japan (2001–2002). He also served as caretaker manager for Spurs in November 1994. As a coach he has won the J.League stage championship (1999 2nd Stage) and the Asian Cup Winners Cup (2000), both with Shimizu S-Pulse. He then worked at Exeter City with no official title to help them stay in the then football Division 3. After this he returned to Japan to manage J.League side Kashiwa Reysol.
Perryman lent his name to a brand of Sports stores in the 1980s which were concentrated in the West London area and sported the Tottenham Hotspur cockerel. There were stores in Ruislip, Greenford and Hayes (Middlesex). A store in Bergen, Norway, also opened in the early 1980s, and that is still running.
Perryman now works as the director of football for Exeter City. On 5 May 2012, while watching Exeter's final game of the 2011-12 season against Sheffield United at St James Park he became unwell and was taken to Derriford Hospital in Plymouth where he underwent successful heart surgery. A month later he revealed that he might have died if it had not been for the instant medical support available at the ground, and he spent three weeks in a coma on life support. He said he wanted to resume his job with Exeter City as soon as he was fit enough.