Objectives Phyllode tumors (PTs) represent a unique entity as mixed fibroepithelial tumors of the breast, which are characterized by a particular histologic appearance, and biologically by frequent local recurrence and low metastatic potential. We aim to study patients with PTs to determine the different histopathological features regarding, tumor grade, margin, hemorrhage, heterologous differentiation, and clinical correlations regarding age, sex, site, local recurrence, and distant metastasis in Sudanese patients. Materials and methods This descriptive retrospective study was carried out on PT specimens obtained from the Pathology Department at National Health Laboratory (NHL), Soba University Hospital (SUH), and Khartoum Teaching Hospital (KTH) during the interval between January 2008 and December 2011. Clinical data were collected from patients’ request forms. The slides were reexamined by two histopathologists using WHO classification of PTs, 2012. The data were analyzed using Statistical Package for Social Sciences. Results The study included 59 specimens diagnosed as PTs. After reexamination of the slides, two cases were excluded, one being a spindle-cell sarcoma and another being a fibroadenoma. The age of the patients ranged from 18 to 80 years. The most common affected age group was 21–40 years. The mean age was 35±1.75 years, and all of them were females. The tumors were found to occur with an equal propensity in either breast. In total, 18 (35.3%) cases were considered histologically benign, 28 (54.9%) cases were considered malignant, and five (9.8%) cases were classified as borderline. Pushing margins were present in all the cases, except three histologically malignant cases, in which the margin was infiltrative. A statistically significant positive relationship was present between tumor grade and presence of hemorrhage (P<0.05). Tumor size was significantly related to histological grade also (P<0.04). However, an insignificant relation was present between local recurrence and tumor grade (P<0.065). Heterologous mesenchymal differentiation was present only in histologically malignant cases. Regional lymph-node involvement was not detected in any of the studied cases. Conclusion In our study, PTs occurred exclusively in females, commonly in the age group 21–40 years, the mean age in our study was 35 years, which is 5 years younger than the mean age reported in the literature, with no reporting of cases below 18 years. Malignant lesions outnumbered the benign lesions. Heterologous differentiation, hemorrhage, large tumor size, and infiltrating tumor margin are positively related to histologically malignant cases. Local recurrence was not significantly related to malignant phenotype, it may reflect the importance of adequate surgical margin.