Under the bilateral approach of the impact of dividend pay-outs with the mediating role of Agency variables, this paper tries to examine its effects on enterprise value, earning per share, stock performance (including Stock Return & Volatility). The mediation test performed by inspecting direct and indirect relationships of dividend pay-out, firm characteristics, and agency factors on a sample size of 130 Pakistani listed firms over eleven years. Results of a study expose the agency factors (such as free cashflows and total institutional ownership structure) role; free cash flow does not mediate the relationship of dividend pay-outs with earning per share and stock volatility separately. Total institutional ownership structure mediates dividend pay-out relation with enterprise value and stock return & volatility. These mixed results contribute to the current literature of finance, specifically in the Pakistani context being an emerging economy.