In 1997 the club celebrated its 50 anniversary. The years since then have been the most momentous since the club was founded, with Wellington's first Shropshire League title in 1998 being follwed by promotion into the new Birmingham and District Premier League for the 1999 season. The first team have finished fifth in both the 1999 and 2000 season.
After gaining promotion to the Birmingham & District Premier League top division in 2002, Wellington CC employed a club professional for the first time. With Chris Rogers' inspiring the home grown talent the team won the championship in 2003 and then retained the title a year later with Benji Hector as the club pro (after Rogers had moved on to play 1st class cricket for Derbyshire CCC).