Right and left upper pulmonary venous flow is usually assessed with monoplane transesophageal echocardiography (TEE) in the transverse imaging plane. Pulmonary venous flow in the transverse imaging plane may be relatively difficult to record because of the larger angle between the pulmonary vein and the transducer beam. To compare the quality of echocardiographically derived Doppler flows of the right and left upper pulmonary veins between the longitudinal and transverse imaging planes with TEE, we performed pulsed-wave Doppler TEE of both upper pulmonary veins in transverse and longitudinal imaging planes in 36 patients with various diseases. We also recorded a quality index for each flow profile and the angle between the transducer beam and the pulmonary vein. The quality index of the left pulmonary venous flow assessed with the longitudinal and transverse imaging planes was similar in 35 (95%) of 36 patients, whereas the longitudinal imaging plane was superior to the transverse plane in one patient (3%). In contrast, the quality index of the right pulmonary venous flow assessed with the longitudinal and transverse imaging planes was similar in only 19 (53%) of 36 patients, whereas in 17 patients (47%) the longitudinal imaging plane was superior to the transverse imaging plane. The quality index had a significant effect on the Doppler flow recordings; suboptimal-quality flow recordings significantly underestimated the pulmonary venous diastolic flow integrals. The left atrium was larger in those patients with unobtainable flows than in those patients with exclusively obtainable flows (p < 0.001). The angle between the sample volume and the right pulmonary vein was larger in the transverse imaging plane than in the longitudinal plane (p < 0.001). In conclusion, the longitudinal imaging plane is generally superior to the transverse imaging plane for assessing right pulmonary venous flow and is recommended for performing a comprehensive assessment of pulmonary venous flow. The ability to obtain quality images and accurate assessment of flow may be related to the size of the left atrium and angle of the pulmonary vein.