<p>This paper investigates a supply chain system for equipment leasing, in which lessors and lessees make decisions regarding the condition of the equipment and associated maintenance services. The goal of maximizing profits within supply chain influences the operation and efficiency of the equipment. Since learning behavior based on maintenance experience affects the lessor’s maintenance strategy, the operating time and utilization rate of the equipment also impact the lessee’s maintenance strategy. We develop decision models that consider both independent and joint decision-making approaches. The results indicate that independent decision-making fails to achieve supply chain coordination. Therefore, a cost sharing strategy and a failure limitation strategy are introduced to achieve coordination. The results demonstrate that both strategies successfully facilitate supply chain coordination. The fixed payment can be used to allocate profits between the two parties and also influences the preference for coordination strategies within the supply chain. It reveals the “best response function” for the frequency of preventive maintenance (PM) at any level of learning, considering the cost of learning behavior. The numerical study illustrates the effects of learning level, leasing period, and coordination strategy on revenue. The results show that the profits of the lessor, lessee, and supply chain increase with the learning level and leasing period. Additionally, the inclusion of a coordination strategy increases the revenue of the supply chain, although the subsidy amount decreases as the rent increases. Furthermore, equipment utilization and operating time positively affect the number of failures, thereby promoting an increase in the frequency of PM.</p>