Background: Lymphoma and multiple myeloma account for a small but significant proportion of all oral malignancies. Oral manifestations of hematopoietic malignancies are sometimes diagnosed with delay as most of them mimic various other diseases like osteomyelitis and periodontal diseases. We present five unusual, challenging cases of head and neck lymphomas and one case of oral myeloma. Methods: In this article, we report six cases, five cases of oral lymphomas, and one oral multiple myeloma case. All cases were initially diagnosed by oral histopathologists and then referred to specialists for further treatment. Results: We report these cases to understand these lesions better, as we saw some worrisome delays in their diagnoses. We aim to raise awareness about these hematopathological diseases among general dentists. Conclusion: It is crucial for the multidisciplinary team members to thoroughly examine the oral cavity for any worrisome lesions like these, as they might be an initial sign of a systemic disease. Pathologists must also be aware of the pitfalls in the interpretation of immunohistochemical sections and the immune profile of a tumor.