Background: Awake craniotomy with intraoperative mapping is the standard of care for gliomas located in language-eloquent regions, enabling maximal safe resection while preserving functional integrity. This study aimed to identify clinical and intraoperative predictors of postoperative language worsening and overall survival in patients undergoing awake surgery for malignant glioma. Methods: In this retrospective multicenter cohort study, 37 patients with malignant glioma in the dominant hemisphere underwent awake craniotomy with intraoperative mapping. Clinical, radiological, intraoperative, and postoperative variables were analyzed. Language outcome was classified as unchanged or worsened. Univariable and parsimonious multivariable logistic regression analyses were used to identify predictors of language worsening. Overall survival was assessed using univariable Cox regression. Results: Postoperative language worsening occurred in six patients (16.2%). Increasing age was associated with higher odds of postoperative language worsening in univariable logistic regression (OR 1.12 per year, 95% CI 1.02–1.23, p = 0.019). Due to the limited number of outcome events, multivariable logistic regression was not performed. In survival analysis, increasing age (HR 1.10, 95% CI 1.05–1.16, p < 0.001) and WHO grade 4 (HR 18.15, 95% CI 3.91–84.19, p < 0.001) were associated with shorter overall survival. No statistically significant association between extent of resection and overall survival was detected in this small cohort. Conclusions: Awake glioma surgery with intraoperative mapping was associated with favorable language outcomes in most patients at the 3-month follow-up. Increasing age was associated with postoperative language worsening in univariable analysis. These findings should be interpreted as exploratory because of the limited sample size and low number of outcome events. Larger prospective studies with standardized longitudinal language assessment are needed.