He had an illustrious career spanning 18 years with the Hokkaido Nippon-Ham Fighters, Yomiuri Giants, and the Chunichi Dragons where he won two Japan Series, two MVP awards in both the Pacific and Central leagues; only one of two people to do so and the first to do it in consecutive seasons. He was an NPB All-Star 11 times. He was also a part of the 2006 and 2009 World Baseball Classic winning Japan sides.
Ogasawara started playing baseball at age 7 playing in the Chiba West Little League. From 1989 he studied at Gyosei International High School in Kisarazu, Chiba Prefecture. When he started at the team he was regarded as a complete no-name and his then coach mentioned that "we were asked to go after a junior middle schooler from the Chiba West Little League and we got the player that no one spoke of, Ogasawara." Up until that point he had been tried at a variety of fielding positions including shortstop, third base and outfield but during high school was converted to be a second baseman and the following year served as a catcher (however Ogasawara admits that catcher was his least favourite position) In his junior year, alongside fellow future pro Tetsuya Kitagawa he finished runner-up in the Chiba prefectural tournament. Although now widely regarded for his power and hitting prowess, Ogaswara failed to register a single home run in the tournament.
Following graduation from high school, Ogasawara was employed with NTT East. He was judged at the time to, even in the worst case, still be of use as a bullpen catcher. He would start life with the team as a catcher and later form a battery with future Hokkaido Nippon Ham Fighters team-mate, Naoyuki Tateishi. In 1996, he took part in the 67th Intercity baseball tournament, playing alongside Nobuhiko Matsunaka with Nippon Steel & Sumitomo Metal Kazusa Magic to reach the best 8.

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