Clinically relevant postoperative pancreatic fistula (CR-POPF) is a significant complication after pancreaticoduodenectomy. CR-POPF is associated with various adverse outcomes, including high mortality rates. Identifying complication predictors for CR-POPF, such as preoperative CT scan features, including pancreatic attenuation index (PAI) and pancreatic duct diameter (PDD), is critical. This systematic review and meta-analysis consolidate existing literature to assess the impact of these variables on CR-POPF risk. Our comprehensive search, conducted in May 2023, covered PubMed, Scopus, Embase, and Web of Science databases. Inclusion criteria encompassed peer-reviewed cohort studies on pancreaticoduodenectomy, focusing on preoperative CT scan data. Case reports, case series, and studies reporting distal pancreatectomy were excluded. The quality assessment of included articles was done using New-Castle Ottawa Scale for cohort studies. Statistical analysis was carried out using Review Manager 5. This study was registered at the International Prospective Register of Systematic Reviews database (PROSPERO) on 12 May 2023 (registration number: CRD42023414139). We conducted a detailed analysis of 38 studies with 7393 participants. The overall incidence of CR-POPF was 24%. Multiple linear regression analyses revealed that PDD and pancreatic parenchymal thickness were significantly associated with CR-POPF. Our systematic review and meta-analysis shed light on CT scan findings for predicting CR-POPF after Whipple surgery. Age, PDD, and pancreatic parenchymal thickness significantly correlate with CR-POPF.