This article presents an extensive Cambridge Structural Database (CSD) analysis on the presence and the role of the halogen bonds in the 5-chlorinated pyrazole motif. The study involved eighty CSD structures (83 .cif) and two new crystals of 1-aryl-5-chloropyrazoles obtained by us with the aim to establish the role of the chlorine atom attached at C-5 of the pyrazole ring both as donor and acceptor of the halogen bond. Different types of halogen contacts appear in 50 % of the investigated molecules. Chlorine atom in the 5-chloropyrazoles structures is involved in Cl···Cl, Cl···Y (Y: O, N, etc.), and Cl···π halogen contacts. The most numerous contacts found were of type Cl···Y (Y: O, N, etc.). The two new 1-aryl-5-chloropyrazole structures reported herein present Cl···O contacts at the sum of the vdW distance. The Cl···O contacts were evaluated also through DFT methods compared with other bonds acting on the same direction.