Covalently bridged pillararene-based oligomers (CBPOs) are formed by covalent bonding of pillararene monomers, and they play a critical role in expanding the multi-disciplinary application of pillararenes due to their excellent molecular complexing ability, specially designed geometry and multifunctional linking groups. This article provides a comprehensive review of the synthesis and applications of CBPOs. The design and synthetic strategies of a series of CBPOs (dimers, trimers, tetramers and others) are first introduced. Many CBPOs with multi-cavities and unique geometry are very attractive and efficient building blocks for constructing novel smart supramolecular polymers (SPs) with different topological structures through host-guest interactions. We describe the methods of constructing various SPs based on CBPOs in detail. Furthermore, the extensive applications of CBPOs and CBPO-based SPs in recognition and detection of ions and organic small molecules, selective adsorption and separation, artificial light-harvesting systems, catalysis, drug delivery systems, and others are systematically introduced. Finally, the future challenges and perspectives for CBPOs are also highlighted.