Skegness Grammar School was founded over 500 years ago by a Lord High Chancellor of England.

[3] The school is organised into four houses all named after historically prominent people or famous Lincolnshire men: Lumley - after Aldred Lumley, 10th Earl of Scarbrough a major local landowner who was responsible for developing Skegness as a major Victorian holiday resort.

Skegness Grammar was the first school in the UK to both apply for and be awarded grant maintained status.

[6] The grant maintained system was dis-established by the new Labour government in 1998 and schools were offered the choice of returning to local education authority funding or opting for foundation status.

The school converted to academy status on 1 September 2012, and is now sponsored by the David Ross Education Trust.