It has often been pointed out by scholars that Chiang Kai-shek’s strategy for the Battle of Shanghai was intended to broaden the battle scope for the purpose of enticing the Imperial Japanese Army (the IJA) to change their offense axis from north-south to east-west China. Although the National Revolutionary Army (the NRA) had suffered heavy casualties in this battle, they managed to drive the IJA’s main force to the south successfully. So this “axis-changing strategy” argument emphasizes that the NRA was successful in terms of strategy. In effect, until now, there has been no consensus on the matter. This article re-visits this particular issue, and concludes that Chiang did intend to launch a war in Shanghai actively, and his strategies were multiple, including preemptive strikes, strategic points defending, and diplomatic negotiations at the beginning. After having failed to initiate combat, his strategy turned to a protracted war. In late September, the protracted war strategy was so extended as to entice the IJA’s main force from North to South China. Near the end of the war, Chiang was so swayed by diplomacy that he could not have chosen his retreat timing well. The NRA however lost this battle tragically in consequence. In sum, Chiang Kai-shek’ strategy for the Battle of Shanghai was constantly changing. The “Axis-changing strategy” was being discussed in the prewar period, but was actually not put into practice in the Battle of Shanghai.