The invention relates to a pen head and penholder assembling system which comprises a pen head conveying chain and a penholder conveying chain. A pen head feeding device and a penholder feeding device are arranged on the left side of the pen head conveying chain and the left side of the penholder conveying chain correspondingly, and an assembling mechanism is arranged at the right end of the pen head conveying chain. A tightening mechanism, a transfer printing mechanism and a drying oven are arranged on the right side of the assembling mechanism. The assembling mechanism comprises a pen head control mechanism and a penholder control mechanism. The pen head control mechanism comprises an assembling clamping claw, a pen head assembling clamping claw cylinder and an assembling lifting rodless cylinder. The penholder control mechanism comprises V-shaped support feet, and the lower ends of the V-shaped support feet are connected to a penholder assembling jacking cylinder. A rubber pressing block is arranged above a penholder, a protruding block is arranged in the middle of the rubber pressing block and presses the penholder, the upper end of the rubber pressing block is connected to a pressing cylinder, and the V-shaped support feet are located in the same vertical plane with the central line of jaws of the assembling clamping claw. Stripping rods are arranged on the front side and the rear side of the protruding block of the rubber pressing block correspondingly and driven by a stripping rod cylinder. The pen head and penholder assembling system can automatically assemble pen heads and penholders.