From the m iddle 16th century to the late 20th century, there had been several tim es ofdram atic changes in Macao’s city character and function. Som e essentials ofthe regulation ofm an-land relationship werereflected in Macao’sdevelopm entand transform a- tion. Macao’s talent show ing itself am ong the num erous ports of Zhejiang, Fujian and Guangdong provinces reflects thatnaturalenvironm entis the absolutely necessary condi- tion for socialdevelopm ent. Macao’s actor as the bridge for the com m unication between theeastern and w estern world showsthatthenaturalenvironm entwon’tbecom etheim pe- tus for socialdevelopm entuntilm an need it. The declination ofthe portofMacao shows thatthe advancem entofthe navigation technology as wellas the enlargem entofthe ship type can resultin the evolvem entofthe m an-land relationship. The difficulties facing by Macao during the transform ation ofits econom ic structure reflectthathum an resource is m ore and m oreim portantin them an-land relationship.Thedeep naturalbrand in Macao’s city im ageand spatialstructure shows thatthedevelopm entofm an-land relationship does notm ean that m an can do withoutnature orignoring the law ofnature, butm eans that m an is deepening the utilization ofnature and the law ofthe nature. Using the regulation ofm an-land relationship to analyze therising and declination of Macao w illfurtherourknowledgeoftheessence ofMacao, and enrich the connotation of geography.