In 1600, during the Battle of Sekigahara Nobuyoshi joined Hidetada's army and fought well in the Battle of Ueda-jo Castle in Shinshu district, so that he distinguished himself as one of the Ueda Shichihon-yari (literally, the seven spears of Ueda).
慶長5年、関ヶ原の戦いにおいて、信吉は秀忠軍の一員として従軍し、信州上田城の戦いにおいて奮戦し、上田七本槍の一人として功名した。