In Korea’s air pollutant inventory, construction machinery is a major emission source in the non-road sector. Since 2004, the Korean government has introduced and reinforced emission regulations to reduce the air pollutants emitted from their diesel engines. Since the engine dynamometer test method used in emission regulations has limitations in reflecting emission characteristics under the diverse working conditions of construction machinery, it is necessary to examine the effectiveness of emission regulations and the validity of the emission factors applied as inputs to the air pollutants inventory. This could be done by evaluating engine operation and emission characteristics under real-world working conditions. In this study, 14 units were selected among the excavators, wheel loaders, and forklifts that represent approximately 90% of the registered construction machines in Korea. They were equipped with a portable emission measurement system (PEMS) to measure gaseous emissions and collect engine data under various real-world working conditions. With the reinforcement of emission regulations for the construction machinery from K-tier3 to K-tier4 in Korea, exhaust after-treatment technologies, such as selective catalytic reduction and diesel oxidation catalyst, were applied. Real world NOx was reduced by approximately 83%, and THC 77% and CO by 73%, respectively. Real world NOx + THC of the K-tier3 machines exceeded the laboratory emission limit, but the K-tier4 machines considerably improved, 20% for excavator (124 kW), 61% for excavator (90 kW), 90% for wheel loader (202 kW) and 21% for Fork-lift (55 kW), despite some differences. The emission factors applied to the air pollutant inventory have been developed using the engine dynamometer test method, but they were considerably underestimated compared with emissions under real-world working conditions. The difference was even larger for the K-tier4 machines. In this study, the possibility of developing emission factor equations that use the engine load factor as a parameter was confirmed by using the engine work 1 g/kW·h segment moving averaging window (MAW) method.