Efficient transplanting has been identified as one of the essential steps towards achieving an increased yield in the farm. However, many factors are affecting these processes such as soil moisture content and the speed of pickup. This study was carried out to investigate the effect of different soil moisture content and pickup speeds on pickup force, balance, resistance, and lump damage during transplanting of seedlings. The results showed that penetration resistance was inversely proportional to the speed and soil moisture content. The highest penetration resistance (38 N) values were recorded under the lowest speed (0.5 mm/s) at the low moisture content; whereas, the lowest penetration resistance was obtained at highest speed (10 mm/s) under high moisture content. The highest pick-up force resistance values were recorded under the lowest speed (0.5 mm/s) at low moisture content than the lowest pick-up force resistance of 1.4 N at (10 mm/s) under the high moisture content. On the other hand, an increase of pick-up force led to a decrease in the pick-up force resistance. The pick-up damage and the pick-up speed are directly proportional—nevertheless, the former increased with a decreasing soil moisture content. The highest pick-up damage values (82%) were observed under the top-most speed (10 mm/s) at high moisture content. It can be concluded that for successful auto-transplanting of seedling the soil condition, the force applied and speed should be taken into consideration. This work will implement an effective seedling-picking performance and basis for the optimal design of end-effectors.