The men's first XV currently compete in Counties 2 Kent - a league at the eighth tier of the English rugby union system.

The club faced many strong teams from 1886 onwards, such as Middlesex Wanderers, Harlequin F.C., Richmond, Eton House, London Scottish and Old Merchant Taylors' FC.

During the 1970s and 80s, Maidstone had become one of the premier clubs in Kent and reached the finals of the county cup for seven years running between 1974 and 1980, winning twice and once again in 1987.

At this point the committee took the decision to appoint a Director of Rugby and new management and coaching structure, the slump was stopped.

Promotion was achieved within three seasons and in 2000, the final of the Kent Cup was lost in the dying moments to National League side, Westcombe Park.

After a Rugby Football Union hearing on 12 January 2011, the club were fined £2000 and found Maidstone guilty of "conduct prejudicial to the interests of the game".

In 2011–12, the club reached the national semi-final of the RFU Senior Vase but lost to eventual winners Wells RFC.

In the Kent cup quarter-final Maidstone beat national three side Westcombe Park to set up a clash with Old Elthamians.

Now competing in the RFU Intermediate Cup, Maidstone have had a brilliant run beating Harrow, Medway, Diss and Chiswick to set up a semi-final with Gloucester-based Coney Hill RFC.

In excess of 7000 supporters travelled to the home of England Rugby to watch Maidstone beat Bridgnorth 31–18 to lift the RFU Intermediate Cup and round off an unbeaten season.