Structured complex silicon components have the potential to develop breakthrough applications in solar cells, biomedical engineering, microfluidics, and MEMS. As silicon is a typical brittle material, ultrasonic vibration diamond cutting has been approved as a promising method to achieve better cutting performance compared to other conventional methods. However, few studies have been conducted on the cutting of structured silicon surfaces by applying high-frequency 1D ultrasonic vibration cutting (UVC), which is expected to possess higher material remove rate. Thus, a detailed understanding of the machining mechanism is yet to be developed. In this study, a series of tests that involve cutting grooves on the silicon surface were first performed by applying UVC and using a single crystal diamond tool. The machined surface and chips were subsequently measured and analysed to evaluate the critical undeformed chip thickness, surface finish, and chip formation. The critical undeformed chip thickness of silicon was found to reach 1030 nm under a certain vibration amplitude. An array of micro grooves was generated at the plastic region with a surface roughness Ra as low as 1.11 nm. Moreover, the material removal and chip formation mechanisms were discussed with the assistance of developing a model used for predicting the length of the tool vibration mark. The results revealed that the micro topography of continuous chips exhibited discontinuous clusters of lines with diameters of dozens of nanometres which was only composed of polysilicon. The model was proved to be able to predict tool marks with extremely low error. Thus, the impact of tool marks on the surface finish can be reduced and even eliminated with help of the model.