Midland Classic was founded in July 2005 by James Boddice and John Mason with a pair of London Central AEC Routemasters operating charter services.

[5] In June 2022, Midland Classic underwent a fares revision which included a joint day-ticket with Select Bus Services and Chaserider.

[13] In June 2023, Rotala reversed the decision to create a multi-operator day ticket with Select Bus Services and Chaserider as part of the Diamond East Midlands Rebranding.

[14] Following this in January 2024, they also withdrew from accepting Staffordshire Knot tickets on the majority of routes, citing its "impact on commercial viability".

Services are also operated on behalf of Leicestershire County Council between Ashby & Loughborough (129) and Leicester & Castle Donington via Coalville (125).