Daylightophil architecture concept is one of the most significant ways to reduce the electrical load consumption in building sector. In deep-plan buildings, or windowless buildings, advanced light transmission systems are used to compensate lighting demands in highperformance architecture theory. The manuscript is to challenge recent innovations in the light transmission systems, the choice of their type should be commensurate with the architectural design, space performance, and design requirements. Light pipes collect sunlight from the outdoor and transmit in the indoor for illumination. This paper presents analysis of daylight simulation of a novel vertical light pipe, which is embedded in an office building to transmit the light in three room, simultaneously. The light pipe (M-type) has two side apertures and one base aperture (multi-apertures) with different diameters (multi-aspect ratio). To analyze this novel vertical light pipe, a comparison was made with a conventional light pipe (S-type) with side-apertures. First, ray-tracing simulations were performed to investigate the penetration of light beams between the two light pipes. In comparison of level of illuminance between two types of light pipes, the efficiencies were evaluated. Daylight simulations were performed continuously throughout the year during daylight hours; in fact, fixed simulation makes it possible to analyze the effect of the sun altitude angle and the azimuth on the level of illuminance and output light beams direction to the spaces. Also, to investigate the effect of altitude and azimuth angles on the efficiency of the pipe (Mtype) and the direction of light output from the side apertures, altitude and azimuths were selected to simulate the design for providing symmetric sunlight on both sides of the building.