His 1996 song "Midnight Shuffle" peaked at number four in the Oricon weekly single charts. The song was the theme of Japanese television drama "Ginrō Kaiki File: Futatsu no Zunō o Motsu Shōnen", in which then-Johnny's Jr. Koichi Domoto played a main role. Kondō appeared on NHK's Kōhaku Uta Gassen annual TV show singing "Midnight Shuffle". From 1998 he went full-time into racing, rarely appearing on TV and not putting out any new songs. His occasional appearances on TV were as a racer or racing commentator. On May 22, 2002, he released a single but it was a cover for his 1985 song "Yoisho". In 2005 Kondō decided to make a full return as a singer for the 25th anniversary of his debut. On December 14, 2005, he released the single "Chōsensya", which means "challenger". He appeared in many TV programs, held dinner shows and went on a limited concert tour. He joined many of his successors such as SMAP, KinKi Kids, V6 and Arashi on their TV shows. On January 25, 2006, Sony released Kondō's tribute album "Matchy Tribute", in which Hitomi Takahashi covered the song "Midnight Shuffle". He also released his greatest hits album "Matchy Best" on February 6, 2006. The album "Matchy Best" debuted at number fifteen on the Oricon album charts. On May 9, 2007, he released his first DVD work, "Kondō Masahiko '07 Valentine's Day in Budokan", which was shot at his live concert at the Nippon Budokan on February 14, 2007. The DVD debuted at number one on the Oricon weekly music DVD charts. In December 2007, it was announced that Kondō collaborated with Johnny's Jr., the five-member of rock band Question?, forming the temporary group "Matchy with Question?" and singing the song "Mezamero! Yasei". The song "Mezamero! Yasei" was used for the ending theme of anime series "" and was released as a CD single on January 23, 2008. The single debuted at number five on the Oricon charts and with the first week sales of around 40,000 copies. Kondō released the single "Banka (Otokotachi no Banka)" on December 23, 2008, and the single "Motto" on December 13, 2009.