Gipps-Kent played "Emmanuel" to Herbert Lom's Napoleon Bonaparte in William Douglas-Home's Betzi at the Haymarket Theatre and on a provincial tour in 1975.

[2] In a 1979 newspaper interview titled Simon's Problem is Time, Gipps-Kent expressed his wish to move on to adult roles, including more Shakespeare, but in spite of his accumulated credentials to date, he had been denied those opportunities.

Due to his "boyish good looks and modest figure", he found himself playing younger characters than his real age, mostly on British television, for the majority of his career.

[2] Gipps-Kent appeared at Wyndham's Theatre and on a provincial tour in Sue Townsend's The Secret Diary of Adrian Mole, Aged 13¾ from 1984 to 1986 as the character "Barry Kent".

[6] His first television appearance was at age 13 in Philip Saville's 1971 O Fat White Woman for BBC's Play for Today, in a story by William Trevor of a teacher who takes pleasure in abusing his students.

Gipps-Kent had the uncredited speaking part of a posh party boy in Quadrophenia (1979), based loosely on the 1973 rock opera of the same name by The Who, and appeared in the Doctor Who (season 17) story The Horns of Nimon.

[9] Gipps-Kent headlined in two Southern Television serials based on books written by British children's authors; Midnight is a Place (1977), by Joan Aiken, and Noah's Castle (1980), by John Rowe Townsend.

As "Chad Boyer", he reunited with Devil's Crown actor John Duttine in his BBC series To Serve Them All My Days (1980), based on the R. F. Delderfield novel.