Oadby Town have won the Leicestershire Senior League eight times and been runners-up seven times. In the 1999/00 season they joined the Midland Football Alliance, and in their first season in this league they were crowned champions.

In the 2002/03 season Oadby Town were FA Vase semi-finalists, losing out to Brigg Town 3-1 on aggregate.

The 2004/05 season saw the club win their first Leicestershire Challenge Cup crown for over 30 years and 3rd in total, beating fellow Midland Alliance side Barwell 2-1 at the Walkers Stadium in Leicester. The 2006/07 season saw Oadby enter the Rolleston Charity Cup for the first time in nine years and winning the competition for a ninth time beating Barwell 2-1 in the final at Holmes Park. The following season saw Oadby retain the Rolleston Charity Cup beating favourites Hinckley United 4-1 in the final. On top of that they won the Leicestershire Challenge Cup for the fourth time beating Friar Lane & Epworth 3-0 at the Walkers Stadium.