Upminster will travel to South Woodford in the 1st round of the Dukes Essex League Cup, on Saturday 22 April.
South will be playing in Division Four in 2023, but the two clubs have enjoyed many great battles at 1st XI level over the years.
The winners of the tie will progress to the 2nd round where they will host either Billericay or Orsett and Thurrock.
The 1st round draw has thrown up a number of local derbys, with Woodford Wells hosting Wanstead and Snaresbrook, Hornchurch playing Rainham, Springfield making the short trip to Chelmsford and Brentwood welcoming Bentley.
The draw for the T20 competition, which the club are back in after an absence over the last few years, will be made next week, but qualifying games will be played on Monday 29 May.