Purpose: To evaluate the prognostic value of preoperative neck lymph node (LN) assessment with $^{18}F$-fluorodeoxyglucose positron emission tomography ($^{18}F$-FDG PET), computed tomography (CT), and magnetic resonance imaging (MRI) in oral cavity squamous cell carcinoma (OSCC) patients with pathologically positive LN. Materials and Methods: In total, 47 OSCC patients with pathologically positive LN were retrospectively reviewed with preoperative $^{18}F$-FDG PET and CT/MRI. All patients underwent surgical resection, neck dissection and postoperative adjuvant radiotherapy and/or chemotherapy between March 2002 and October 2010. Histologic correlation was performed for findings of $^{18}F$-FDG PET and CT/MRI. Results: Thirty-six (76.6%) of 47 cases were correctly diagnosed with neck LN metastasis by $^{18}F$-FDG PET and 32 (68.1%) of 47 cases were correctly diagnosed by CT/MRI. Follow-up ranged from 20 to 114 months (median, 56 months). Clinically negative nodal status evaluated by $^{18}F$-FDG PET or CT/MRI revealed a trend toward better clinical outcomes in terms of overall survival, disease-free survival, local recurrence-free survival, regional nodal recurrence-free survival, and distant metastasis-free survival rates even though the trends were not statistically significant. However, there was no impact of neck node standardized uptake value ($SUV_{max}$) on clinical outcomes. Notably, $SUV_{max}$ showed significant correlation with tumor size in LN (p < 0.01, $R^2$ = 0.62). PET and CT/MRI status of LN also had significant correlation with the size of intranodal tumor deposit (p < 0.05, $R^2$ = 0.37 and p < 0.01, $R^2$ = 0.48, respectively). Conclusion: $^{18}F$-FDG PET and CT/MRI at the neck LNs might improve risk stratification in OSCC patients with pathologically positive neck LN in this study, even without significant prognostic value of $SUV_{max}$.