This research investigates whether market pioneering advantage in the previous-generation market can be sustained in the successive-generation market of a product category. The empirical data reported in the current research demonstrate that a market pioneer in the previous-generation market cannot sustain its market share leadership unless it also pioneers the successive-generation market. Also, pioneering the successive generation market with a new brand rather than an extant brand generates a greater market share reward for a market pioneer in the previous-generation when the ideal attribute combination of a successive-generation product is ambiguous. When the ideal attribute combination is unambiguous, the use of an extant brand rather than a new brand contributes to increased market share rewards for a market pioneer in the previous-generation market which enters first in the successive-generation market. The authors conclude that continuous market pioneering is necessary in the multi-generations of a product-market because perceived innovativeness mediates the order of entry effect.