This manual covers the Chief models produced from 1999 to 2001. The Chief represents a significant part of heritage, a brand renowned for its iconic styling and powerful V-twin engines. These motorcycles are characterized by their classic American cruiser design, air-cooled V-twin engines, and robust construction, offering a distinctive riding experience rooted in American motorcycling history. This comprehensive guide is designed for owners, independent repair shops, and motorcycle technicians seeking detailed information to maintain and service these specific models. This workshop repair and service manual provides in-depth coverage of essential maintenance procedures, including interval service, renewal service, and detailed maintenance procedures. It also offers extensive repair guidance for various systems, such as engine components (carburetor rebuild, rocker box gasket replacement), drivetrain (clutch disk inspection and replacement, transmission rebuild), electrical systems, and chassis components. The manual includes electrical troubleshooting, pre-delivery inspection, and specific technical data, empowering users with the knowledge to perform accurate repairs and ensure the longevity and optimal performance of their Chief motorcycle.