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We address the problem of two-dimensional (2-D) shape representation and matching in presence of self-intersection for large image databases. This may occur when part of an object is hidden behind another part and results in a darker section in the gray level image of the object. The boundary contour of the object must include the boundary of this part which is entirely inside the outline of the object. The curvature scale space (CSS) image of a shape is a multiscale organization of its inflection points as it is smoothed. The CSS-based shape representation method has been selected for MPEG-7 standardization. We study the effects of contour self-intersection on the curvature scale space image. When there is no self-intersection, the CSS image contains several arch shape contours, each related to a concavity or a convexity of the shape. Self intersections create contours with minima as well as maxima in the CSS image. An efficient shape representation method has been introduced in this paper which describes a shape using the maxima as well as the minima of its CSS contours. This is a natural generalization of the conventional method which only includes the maxima of the CSS image contours. The conventional matching algorithm has also been modified to accommodate the new information about the minima. The method has been successfully used in a real world application to find, for an unknown leaf, similar classes from a database of classified leaf images representing different varieties of chrysanthemum. For many classes of leaves, self-intersection is inevitable during the scanning of the image. Therefore the original contributions of this paper is the generalization of the curvature scale space representation to the class of 2-D contours with self-intersection, and its application to the classification of Chrysanthemum leaves.