Background: “Windswept” deformity (WSD) consists of a non-frequent condition in which the patient presents a valgus deformity in one knee and a varus deformity in the other. We performed a review of the available literature to aggregate the accessible data on the outcomes of bilateral knee arthroplasty in patients with WSD and to discuss the surgical challenges that this condition might pose. Methods: A systematic review of the literature following the PRISMA guidelines was conducted. The relevant studies between 1979 and 2021 were identified. Four studies with a total of 68 patients were included for analysis. The mean follow-up for varus knees was 3.3 years, 3.1 years for valgus knees. The quality and rigor of the included studies was assessed using the Methodological index for non-randomized studies (MINORS). Results: All the studies reported improvement in knee function following knee replacement surgery, and a reduction in axial deviation of both knees, with similar results in valgus and varus knees in terms of patient satisfaction. The most relevant data were that unicompartmental knee arthroplasty (UKA) allowed for limited axial correction with slightly inferior functional results. Kinematic alignment (KA) allowed for similar results in both knees. Conclusion: The present review shows how satisfactory results can be achieved in both knees in patients with WSD and osteoarthrosis (OA). However, the operating surgeon should be aware of the importance of the implant choice in terms of functional outcomes. In the absence of extra-articular deformities, calipered KA total knee arthroplasty (TKA) can be performed on both knees with good axial correction and functional outcome. Level of evidence: II —Systematic review of cohort studies.