Language fMRI has become an integral part of the planning process in brain surgery. However, fMRI may suffer from confounding factors both on the patient side, as well as on the provider side. In this study, we investigate how patient-related confounds affect the ability of the patient to perform language fMRI tasks (feasibility), the task sensitivity from an image contrast point of view, and the anatomical specificity of expressive and receptive language fMRI protocols. 104 patients were referred for language fMRI in the context of presurgical procedures for epilepsy and brain tumor surgery. Four tasks were used: (1) a verbal fluency (VF) task to map vocabulary use, (2) a semantic description (SD) task to map sentence formation/semantic integration skills, (3) a reading comprehension (RC) task and (4) a listening comprehension (LC) task. Feasibility was excellent in the LC task (100%), but in the acceptable to mediocre range for the rest of the tasks (SD: 87.50%, RC: 85.57%, VF: 67.30%). Feasibility was significantly confounded by age (p = 0.020) and education level (p = 0.003) in VF, by education level (p = 0.004) and lesion laterality (p = 0.019) in SD and by age (p = 0.001), lesion laterality (p = 0.007) and lesion severity (p = 0.048) in RC. All tasks were comparable regarding sensitivity in generating statistically significant image contrast (VF: 90.00%, SD: 92.30%, RC: 93.25%, LC: 88.46%). The lobe of the lesion (p = 0.005) and the age (p = 0.009) confounded contrast sensitivity in the VF and SD tasks respectively. Both VF and LC tasks demonstrated unilateral lateralization of posterior language areas; only the LC task showed unilateral lateralization of anterior language areas. Our study highlights the effects of patient-related confounding factors on language fMRI and proposes LC as the most feasible, less confounded, and efficiently lateralizing task in the clinical presurgical context.