Drilling, as the initial stage of exploitation in open-pit mining, has a significant effect on subsequent mining stages. Any failure in a drilling machine stops the drilling operation and, as a result, all following operational phases come to a halt. The drilling system is the most important part of the drilling operation. This study selected two new rotary-type drilling machines (A and B) in Sarcheshmeh Copper Mine in Iran as a case study to perform a reliability and availability analysis of their drilling systems. The drilling system was divided into three independent subsystems; drill string, rotary head, and mast. The reliability modeling used a reliability block diagram and Monte Carlo simulation. Reliability and availability were evaluated, and the importance of each subsystem estimated. A preventive maintenance schedule was proposed using weighed reliability allocation to achieve the reliability target. The results show the mast is the most reliable subsystem. Importance measure analysis indicates the drill string and rotary head are the most critical subsystems of machines A and B, respectively. Finally, under the proposed maintenance policy, the reliability of the drilling systems of machines A and B is improved.