Visuo-spatial neglect (often simply referred to as “neglect”) is a complex poststroke medical syndrome which may be assessed by means of a series of drawing-based tests. Based on a novel analysis of a test battery formed from established pencil-and-paper tests, the aim of this study is to develop an automated assessment system which enables objectivity, repeatability, and diagnostic capability in the scoring process. Furthermore, the novel assessment system encapsulates temporal sequence and other “dynamic” information inherent in the drawing process. Several approaches are introduced in this paper and the results compared. The optimal model is shown to produce significant agreement with the score for drawing-related components of the Rivermead Behavioural Inattention Test, the widely accepted standardised clinical test for the diagnosis of neglect, and, more importantly, to encapsulate data to enable an enhanced test resolution with a reduction in battery size.