Significant strides have been taken in the structural design of fibrous composites in recent decades. Early detection of material degradation and damage in such materials is crucial for various industrial applications, yet poses challenges. Second harmonic Lamb waves have demonstrated their superior sensitivity to microstructural defects, making them an effective tool for structural health monitoring (SHM). However, understanding of the second harmonic Lamb wave generation and propagation in composite laminates remains inadequate due to the complexities introduced by material anisotropy and damping, which impede the practicality of SHM applications. This study investigates the cumulative second harmonic Lamb waves in composite laminates at low frequencies, considering both material anisotropy and damping. Theoretical analyses were carried out to explore how anisotropy and damping affect the generation and propagation of second harmonic Lamb waves. A nonlinear material constitutive model was proposed. It was used to conduct numerical simulations that verified the properties of second harmonic Lamb wave generation and propagation at different wave propagation angles, with a focus on the cumulative effect. Experiments were carried out to further validate the properties of the second harmonic Lamb waves in a carbon fiber reinforced panel. The findings indicate that the Lamb waves propagating at 0° showcase exceptional cumulative effect, rendering them suitable for SHM applications. Additionally, material damping induces a cumulative second harmonic Lamb wave with an initial increase followed by a decrease, creating a predictable “sweet” zone of larger amplitude that is easy to measure for SHM applications. The elucidation of the generation and propagation characteristics of the second harmonic Lamb waves provides guidance for structural damage detection and monitoring applications.