Cyclin-dependent kinase 2 (CDK2) is a well-established target for anti-cancer therapies and, more recently, non-hormonal male contraception, given its pivotal role in cell cycle regulation and meiosis. However, the development of effective, FDA-approved CDK2 inhibitors has been hindered by the challenge of achieving selectivity, particularly over the closely related kinase CDK1. Allosteric inhibitors offer a promising alternative by targeting non-catalytic binding sites, thus providing the potential for greater selectivity and fewer off-target effects. Recent crystallographic studies have identified four distinct allosteric pockets on CDK2, providing new avenues for drug development. Notable allosteric ligands, such as EF-3-006, demonstrate both potent CDK2 binding (KD of 18 nM ) and impressive selectivity over CDK1, along with functional effects like meiosis arrest in mouse testicular explants, highlighting their potential for non-hormonal contraception. Despite these promising findings, allosteric kinase inhibitors remain an underexplored area of research. Targeting these newly discovered allosteric pockets may enable the development of selective, efficacious therapies for cancer and contraception, overcoming the challenges faced by traditional ATP site inhibitors.