The first five preliminary designs proposed demolishing the east and west wings of the old college and building an extensive new development to the south, retaining the existing chapel. The first design was an open quadrangular plan. The second design was an H-plan. The third was a cross-plan and the fourth and fifth designs were a closed quadrangular plan. These designs were illustrated by block plans and bird’s-eye views. They were delivered to the client on 16 May 1811 with a general estimate of £8,000. All of the schemes were rejected because they were deemed too extravagant and too expensive.

The alternative drawings show a variation of transom and mullion windows designed to echo the original seventeenth-century windows of the College, as seen in the survey drawings of section 1. Furthermore, brick pilasters provide a reference to the Gothic buttresses of the old chapel. These designs for incorporating elements of the original architecture continue to be developed in later drawings.

George Allen Underwood is recorded in the Day Books as having 'drawn plans for Dulwich College' on Wednesday 27^th-30^th March and Tuesday 2^nd-8^th April 1811. On Monday 1^st April Underwood took the dimensions of Sir Bourgeois' pictures, presumably so to plan wall space within the galleries. George Bailey and George Allen Underwood are the most frequently mentioned pupils in the Day Book at this stage of designing. It seems Underwood worked mostly on plans and Bailey on perspectives.