Popliteal swelling is a common complaint seen in the practice of orthopaedics. Although imaging is useful to aid in the diagnosis of popliteal swelling pre-operatively, definitive diagnosis is often obtained post-operatively through histopathological report of the swelling. Baker’s cyst arises medially and hence usually spares the posterolaterally located neurovascular bundle until it becomes larger in size. A thrombosed aneurysm can mimic that of Baker’s cyst on computed tomography (CT) imaging in view of its location and the absence of contrast within the lesion. Diagnosis of a popliteal swelling with neural or vascular compression is not as straightforward and surgeons should be well aware that intra-operative findings may differ from diagnosis made preoperatively. Meticulous exploration is pertinent in identifying the origin of the swelling and structures related to it. MRI imaging of the swelling should be done preoperatively whenever possible.