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Objective: This study assessed dynamic contrast-enhanced (DCE)-MRI and intravoxel incoherent motion diffusion-weighted imaging (IVIM DWI) parameters to prospectively predict survival outcomes in participants with advanced hepatocellular carcinoma (HCC) who received lenalidomide, a dual antiangiogenic and immunomodulatory agent, as second-line therapy in a Phase II clinical trial. Materials and methods: Forty-four participants with advanced HCC who had progression after sorafenib as first-line treatment were prospectively enrolled. Pretreatment MRI parameters—obtained from DCE-MRI (peak, slope, AUC, K^trans, K_ep, and V_e), apparent diffusion coefficient (ADC), and IVIM DWI (pure diffusion coefficient (D), pseudodiffusion coefficient (D*), and perfusion fraction (f))—were derived from the largest hepatic tumor. The Cox model was used to investigate the associations of the parameters with progression-free survival (PFS) and overall survival (OS). Results: Median PFS and OS were 2.3 and 8.0 months, respectively. Univariate analysis showed that participants with a high slope (<i>p</i> = 0.024), K_ep (<i>p</i> < 0.001), and ADC (<i>p</i> = 0.018) values had longer PFS than those with low values; participants with a small tumor size (<i>p</i> = 0.006), high slope (<i>p</i> = 0.01), ADC (<i>p</i> = 0.015), and f (<i>p</i> = 0.012) values had longer OS than those with low values did. Cox multivariable analysis revealed that K_ep (<i>p</i> < 0.001) and ADC (<i>p</i> = 0.009) remained independent predictors of PFS; slope (<i>p</i> = 0.003) and ADC (<i>p</i> = 0.009) remained independent predictors of OS. Moreover, K_ep and slope were still significant after Bonferroni correction was performed (<i>p</i> < 0.005). Conclusion: Both pretreatment DCE-MRI and IVIM DWI parameters, especially slope and ADC, may predict PFS and OS in participants with HCC receiving lenalidomide as second-line therapy.