A novel micropipet technique was developed to quantify the dewetting dynamics of individual microsphere particles by emulsified viscous crude oil drops in aqueous media. This technique allowed dynamic microscale receding contact angles of water to be measured in situ for solid–oil–water systems. System parameters, including modification of glass microspheres and characteristics of oil drops, were varied to study their effect on dewetting dynamics of the systems. Increasing solvent dosage in viscous oil was found to decrease static receding contact angle of water for clean and bitumen-treated glass surfaces, but showed a negligible effect on static receding contact angle for ethyl cellulose (EC)-treated glass surface. Interestingly, dynamic dewetting behavior exhibited a strong dependence on surface modification and the addition of solvent to viscous oil. No dewetting dynamics was observed for clean hydrophilic glass surface. For bitumen- or EC-treated glass surfaces, more rapid dewetting dynamics of water were determined with increasing addition of solvent to viscous oil. Both de Gennes viscous dissipation hydrodynamic and the Blake/Haynes molecular-kinetic models were developed for the current system to understand the observed dynamic dewetting characteristics.A novel micropipet technique was developed to quantify the dewetting dynamics of individual microsphere particles by emulsified viscous crude oil drops in aqueous media. This technique allowed dynamic microscale receding contact angles of water to be measured in situ for solid–oil–water systems. System parameters, including modification of glass microspheres and characteristics of oil drops, were varied to study their effect on dewetting dynamics of the systems. Increasing solvent dosage in viscous oil was found to decrease static receding contact angle of water for clean and bitumen-treated glass surfaces, but showed a negligible effect on static receding contact angle for ethyl cellulose (EC)-treated glass surface. Interestingly, dynamic dewetting behavior exhibited a strong dependence on surface modification and the addition of solvent to viscous oil. No dewetting dynamics was observed for clean hydrophilic glass surface. For bitumen- or EC-treated glass surfaces, more rapid dewetting dynamics of water were determined with increasing addition of solvent to viscous oil. Both de Gennes viscous dissipation hydrodynamic and the Blake/Haynes molecular-kinetic models were developed for the current system to understand the observed dynamic dewetting characteristics.