It was until 1963 that the club won its first major honours winning the Leicestershire Senior Cup for the first time beating Newfoundpool WMC in the final.

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 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.

Oadby managed a successful season with a decent run in the FA Vase, being the only team from below Step 5 to reach the 5th Round, losing to Staveley Miners Welfare.