In this work, we investigate and compare the condensation behavior of hydrophilic, hydrophobic, and biphilic microgrooved silicon samples etched by reactive ion etching. The microgrooves were 25 mm long and 17-19 μm deep with different topologies depending on the etching process. Anisotropically etched samples had 30 μm wide rectangular microgrooves and silicon ridges between them. They were either left hydrophilic or covered with a hydrophobic fluorocarbon or photoresist layer. Anisotropically etched samples consisted of 48 μm wide semicircular shaped microgrooves, 12 μm wide silicon ridges between them, and a 30 μm wide photoresist stripe centered on the ridges. The lateral dimensions were chosen to be much smaller than the capillary length of water to support drainage of droplets by coalescence rather than droplet sliding. Furthermore, to achieve a low thermal resistance of the periodic surface structure consisting of water-filled grooves and silicon ridges, the trench depth was also kept small. The dripped-off total amount of condensate (AoC) was measured for each sample for 12 h under the same boundary conditions (chamber temperature 30 °C, cooling temperature 6 °C, and relative humidity 60%). The maximum increase in AoC of 15.9% (9.6%) against the hydrophilic (hydrophobic) reference sample was obtained for the biphilic samples. In order to elucidate their unique condensation behavior, in situ optical imaging was performed at normal incidence. It shows that the drainage of droplets from the stripe's surface into the microgrooves as well as occasional droplet sliding events are the dominant processes to clear the surface. To rationalize this behavior, the Hough Circle Transform algorithm was implemented for image processing to receive additional information about the transient droplet size and number distribution. Postprocessing of these data allows calculation of the transient water load on the stripe's surface, which shows an oscillatory behavior not previously reported in the literature.