Abstract Introduction/Objective Phyllodes tumor (PT), a rare fibroepithelial breast lesion, affects around 1% of breast tumors, primarily in women aged 40–50 years old. The interpretive subjectivity, histological overlap, and limited molecular predictors, necessitate further investigation into their pathogenesis. Prognosis relies on WHO grading based on stromal proliferation. Malignant-PTs are rare and challenging to diagnose, posing a diagnostic challenge with breast sarcomas and metaplastic carcinomas. The study aims to highlight morphological features of malignant-PTs and their correlation on patients’ survival and prognosis. Methods/Case Report Retrospective single-institute study of 33 women who were diagnosed with malignant-PT according to WHO criteria and underwent excision were identified from database spanning 2005-2024. Clinical and pathologic characteristics including biopsy results, histological features, imaging findings, and survival outcomes were analyzed statistically using Kaplan-Meier method. Results (if a Case Study enter NA) Patients aged 28-72 years underwent excision, with a mean of 50 years and tumor sizes ranging 1.1-34 cm with a mean of 11.5 cm. The majority (19 cases) were classified as pT stage I or II, with 14 cases at more advanced stages. Malignant heterologous elements were found in 10 cases (30%). Positive margins were noted in 12 excisions (36%). Besides tumor recurrence in 3 cases (9%) within 33 months post-excision, metastasis was observed in 8 cases, occurring between 4-60 months post-excision. Six patients died from metastasis within 11-62 months post-diagnosis. Conclusion The presence of negative margins and appropriate treatment was associated with a lower risk of recurrence and metastasis. However, they were not linked to enhance survival rates. Survival was primarily correlated to the absence of heterologous components and PT’s staging.