Initially operating as South Eastern, on 13 October 1996 Connex South Eastern commenced operating the franchise having beaten bids from a Management/FirstBus consortium, GB Railways and Stagecoach. In December 2002, after the franchise ran into financial trouble, the Strategic Rail Authority agreed to bail it out with a £58 million injection, with the end date brought forward from 2011 until 2006. However continuing poor financial management resulted in the Strategic Rail Authority deciding to strip Connex of the franchise in June 2003. Connex South Eastern continued to operate the franchise until 8 November 2003.
On 9 November 2003 South Eastern Trains, a subsidiary company of the SRA, took over the franchise for a planned 18 months. It took on all the leased rolling stock and most of Connex staff including senior management. In the event it took over two years to relet the franchise to a private company.
In December 2003 the SRA announced that Danish State Railways/Stagecoach, FirstGroup, Govia and MTR/Sea Containers had been shortlisted to bid for the replacement Integrated Kent franchise that would also incorporate services on High Speed 1 out of St Pancras. In November 2005 the Department for Transport announced Govia had been awarded the franchise with the services operated by South Eastern Trains transferred to Southeastern on 1 April 2006. The franchise was let for an initial eight years, with a two-year option dependent on performance targets being met. In December 2008, as part of the franchise agreement, operation of Redhill to Tonbridge Line services passed to Southern. High Speed 1 services began on 14 December 2009. Having met the performance criteria, in March 2011 the DfT granted Govia a two-year franchise extension until March 2014. Following the DfT's review after the cancellation of the InterCity West Coast franchise process, extensions were granted to the franchises due for renewal with Southeastern's franchise extended until June 2018. It has since been extended a number of times and was scheduled to conclude on 31 March 2020 however the direct award from the DfT extended the franchise to 16 October 2021.
Future
In June 2017 the DfT announced a shortlist of: Abellio/East Japan Railway Company/Mitsui consortium; incumbent Govia; Stagecoach; and Trenitalia for the next franchise, which was once again named the South Eastern franchise. In August 2017, Trenitalia withdrew citing a desire to concentrate its resources on its bid for the West Coast Partnership. In February 2018, it was announced that Alstom would take a 20% shareholding in the Stagecoach company. In April 2019, Stagecoach was disqualified from the bidding because they did not meet pensions rules. The franchise was extended a number of times however on 7 August 2019, the franchise competition was cancelled and the DfT instead took up a further extension and the current franchise was due to cease on 31 March 2020, until a new contract was agreed on 30 March 2020, running for up to 2 years.