<p>The optimal surgical timing for synchronous colorectal liver metastases (sCRLM) regarding simultaneous versus staged resection remains controversial. This systematic review and meta-analysis aimed to evaluate whether the surgical approach influences the likelihood of achieving “Textbook Outcome” (TO), a composite metric representing an ideal postoperative course. A comprehensive literature search was conducted in PubMed, MEDLINE, and The Cochrane Library in November 2025 following PRISMA guidelines. Studies comparing simultaneous versus staged resection for sCRLM and reporting TO were included. Data were synthesized using a random-effects model to calculate pooled Odds Ratios (OR). Three retrospective cohort studies comprising 1,542 patients were included in the quantitative synthesis. Patients undergoing simultaneous resection demonstrated significantly lower odds of achieving TO compared to those undergoing staged resection (pooled OR 0.38, 95% CI 0.18–0.81; <i>p</i> = 0.01). Sensitivity analysis excluding the study with the largest sample size eliminated statistical heterogeneity (I² = 0%) and reinforced the superiority of the staged approach (OR 0.24; <i>p</i> &lt; 0.00001). Furthermore, failure to achieve TO in simultaneous cases was associated with delays in return to intended oncologic therapy. Staged resection is associated with a significantly higher likelihood of achieving Textbook Outcome compared to simultaneous resection. While simultaneous resection may be considered for highly selected patients, a staged approach generally maximizes the probability of an ideal surgical and oncologic outcome.</p>