In recent years, inkjet printing has emerged as a promising advanced fabrication technology in the field of electronics, offering remarkable advantages in terms of cost-effectiveness, design flexibility, and rapid prototyping. For these reasons, inkjet printing technology has been widely adopted in various applications, including printed circuit board fabrication, sensor development (e.g., temperature, humidity, and pressure sensing), and antenna and filter production, up to the microwave frequency range. The present paper is focused on the investigation of a methodology based on Monte Carlo simulations for quantitatively assessing the influence of fabrication tolerances on the performance of inkjet-printed microwave devices. In particular, the proposed methodology is applied to an inkjet-printed hairpin band pass filter specifically tailored for operation in the L band (i.e., from 1 GHz to 2 GHz). The initial design phase involved the use of computer aided design (CAD) software to optimize the geometric dimensions of the designed filter to closely match the desired performance specifications in terms of bandwidth, insertion loss, and return loss. Later, a Monte Carlo analysis was conducted to evaluate the propagation of tolerances in the fabrication process throughout the design and to estimate their effects on device performance. The fabrication process exploited the advanced capabilities of the Voltera inkjet printer, which was used to deposit a silver-based conductive ink on a commercial Rogers substrate. The device’s performance was evaluated by comparing the simulated scattering parameters with those measured on the developed filter using a vector network analyzer (VNA), thus ensuring accurate validation of real-world performance.