Simple Summary Canine cutaneous mast cell tumors have variable rates of recurrence and metastasis. We sought to evaluate how various prognostic factors affect survival, recurrence, and metastasis in a retrospective study of 90 dogs with cutaneous mast cell tumors treated with surgery and vinblastine chemotherapy. Factors evaluated included age, breed, grade, margins, local tumor control, mitotic count, lymph node metastasis, response to vinblastine chemotherapy in the gross disease setting, and timing of vinblastine in relation to surgery. Eighteen dogs received neoadjuvant vinblastine, and no dogs progressed locally before surgery. The use of neoadjuvant vinblastine was associated with a higher chance of local recurrence (p = 0.03) but not survival. Significantly shorter survival times were found for high-grade tumors (p < 0.001), grade 3 tumors (p < 0.001), and tumors with a mitotic count of >5 (p < 0.001). Dogs with grade 2/low grade cutaneous mast cell tumors lived longer than those with grade 2/high grade tumors (p < 0.001). Both grading systems and mitotic count were prognostic for survival in this population of dogs, supporting the need for standard reporting of histopathologic findings. Neoadjuvant chemotherapy can be effective in downsizing canine cutaneous mast cell tumors but does not influence survival. Abstract Objective: Canine cutaneous mast cell tumors (cMCTs) have variable rates of recurrence and metastasis. We evaluated how various prognostic factors affect survival, recurrence, and metastasis in dogs with cMCT who underwent surgery and vinblastine chemotherapy. Animals: 90 dogs with cMCT treated with surgery and vinblastine at a veterinary referral institution were included. Methods: Medical records were retrospectively reviewed. Prognostic factors were evaluated. Results: Most dogs (94%) had grade 2 or 3 cMCTs. Neoadjuvant vinblastine was used in 18 dogs, and none progressed locally before surgery. The use of neoadjuvant vinblastine was associated with a higher chance of local recurrence (p = 0.03) but not survival. Shorter survival times were found for tumors that were high-grade (p < 0.001), grade 3 (p < 0.001), or a MC of >5 (p < 0.001). Dogs with grade 2 tumors that were low-grade lived longer than those with high-grade tumors (p < 0.001). Histologic tumor-free margins and the ability to achieve local tumor control were not associated with outcome. Clinical Relevance: Both grading systems and MC were prognostic for survival in this population of dogs, supporting the need for the standard reporting of histopathologic findings. Neoadjuvant chemotherapy can be effective in downsizing cMCTs but does not influence survival. These findings are consistent with previous publications, showing the benefits of a more modern population of patients, surgical treatments, and histopathologic assessments.