Gordon Brasted Trophy holders Takeley have a tricky start to the defence of their title, as they travel to East London to face Barkingside at Cricklefield in the first round.
Redbridge will face local rivals Woodford Town 2017 and Southend Manor host FC Romania in the other pick of the first round ties.
Incredibly, as well as being drawn together in the Errington Challenge Cup, West Essex will play Basildon United at Mayesbrook also in the Gordon Brasted Trophy.
Potential second round local derbies could see Great Wakering meet Hullbridge if the visitors beat Sporting Bengal, Burnham could play Southend Manor in another South-East Essex derby clash.
First Round: (Ties to be played week commencing 9th October):
Hullbridge v Sporting Bengal United
Southend Manor v FC Romania
Tower Hamlets v Stansted
Barkingside v Takeley
Woodford Town 2017 v Redbridge
Second Round: (Ties to be played week commencing 24th October):
Burnham Ramblers v Southend Manor OR FC Romania
Hackney Wick v Barkingside OR Takeley
Sawbridgeworth Town v Tower Hamlets OR Stansted
Great Wakering Rovers v Hullbridge Sports OR Sporting Bengal United
Waltham Forest v Woodford Town 2017 OR Redbridge
Ilford v Enfield 1893
Wadham Lodge v Clapton
West Essex v Basildon United
Quarter-Finals: (Ties to be played week commencing 13th November):
Waltham Forest OR Woodford Town 2017 OR Redbridge v Ilford OR Enfield 1893
Sawbridgeworth Town OR Tower Hamlets OR Stansted v Burnham Ramblers OR Southend Manor OR FC Romania
Hackney Wick OR Barkingside OR Takeley v Great Wakering Rovers OR Hullbridge Sports OR Sporting Bengal United
Wadham Lodge OR Clapton v West Essex OR Basildon United
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