Provided are a measurement system, a measurement method, and a measurement program capable of measuring the amount of a drug solution that fills a needle-shaped recess of a mold or the amount of a drug after the filled drug solution is dried in a non-destructive manner with high accuracy before a micro-needle array is separated from the mold. According to a preferred aspect, there is provided a measurement system (1) that measures the volume of a drug solution that fills a needle-shaped recess of a mold. A measurement unit (10) of the measurement system (1) measures respective heights of a plurality of measurement points which are stored in a storage unit (20) and are preset on a plane parallel to the mold, in a direction orthogonal to the plane. A surface shape calculation unit (30) calculates a three-dimensional shape of the surface of the drug solution on the basis of the heights of the plurality of measurement points measured by the measurement unit (10). A volume calculation unit (50) calculates the volume of the drug solution that fills the needle-shaped recess on the basis of the three-dimensional shape of the surface of the drug solution calculated by the surface shape calculation unit (40) and the shape of the needle-shaped recess of the mold.