The former youth coach at Crewe Alexandra denied the eight counts when he appeared at Chester Crown Court.
The charges all relate to allegations of abuse between 1981 and 1986.
Mr Bennell, 63, wearing a blue polo neck shirt and appearing via videolink from HMP Woodhill, in Milton Keynes, answered "not guilty" to all the charges as they were put to him.
The ex-coach, who also worked at Manchester City, Stoke City and junior teams in north-west England and the Midlands, was remanded into custody until 20 March.
Owen Edwards, prosecuting, told the court the alleged victim "preserves his anonymity".
Former football coach Barry Bennell has pleaded not guilty to eight charges of sexual assault against a boy under 16.