Gromov (2001) and Sturm (2003) proved that any four points in a CAT(0) space satisfy a certain family of inequalities. We call those inequalities the ⊠-inequalities, following the notation used by Gromov. In this paper, we prove that a metric space X containing at most five points admits an isometric embedding into a CAT(0) space if and only if any four points in X satisfy the ⊠-inequalities. To prove this, we introduce a new family of necessary conditions for a metric space to admit an isometric embedding into a CAT(0) space by modifying and generalizing Gromov’s cycle conditions. Furthermore, we prove that if a metric space satisfies all those necessary conditions, then it admits an isometric embedding into a CAT(0) space. This work presents a new approach to characterizing those metric spaces that admit an isometric embedding into a CAT(0) space.