The ability of entrepreneurs to arrange working capital is the key to maximizing the profitability of small- and medium-sized enterprises and the wealth of entrepreneurs. The study investigates the correlation between entrepreneurs’ working capital management and the profitability of SMEs listed on six Gulf Cooperation Council (GCC) stock exchanges between 2019 and 2020. The secondary data is collected from the financial statements of SMEs listed on the six GCC stock exchanges. Actual sample for the research study was a total of 136 small- and medium-sized enterprises selected using purposive sampling methods. Four research models were considered in this analysis, all ending up affecting gross profits. The selected entrepreneurial SMEs were listed on six different Gulf Cooperation Council stock exchanges during 2019–2020. The fixed financial assets ratio, financial debt ratio, and company size are used as control variables and data were analyzed using multiple regression. The research results demonstrate that there is a statistically significant negative correlation between profitability measured by gross profit and cash cycle and the components of the cash cycle (including days of accounts receivable and days of inventory). The study further reveals that there is no significant correlation between gross profit and days of accounts payable.