The present work is focused on the investigation of tetra-anti-chiral structures by means of numerical and analytical methods. Specimens were evaluated under compressive load using analytical and numerical methods. The paper summarizes a theoretical solution for the estimate of Poisson’s ratio and the plateau force. The models can handle structures with various configurations, such as the radius of the connection node, lengths, and thickness of the ligaments. A section dedicated to the evaluation of the buckling load is included to extend the investigation of the behavior under compressive loads. The theoretical model is based on Euler’s formula, and a series of amendments are performed to adapt the formula to the analysis of chiral structures. Throughout the paper, theoretical results are compared with results from the simulations to validate the principles stated. Two sets of numerical models were developed: a fully 3D model using hexahedral finite elements and a 2.5D model using a beam finite element model. An overall comparison of results is presented, showing a good agreement between datasets. The present work might set the background for future activities, allowing for a selection of individual investigation methods.