Tomorrow night’s BBC Essex Senior Cup tie pits Boro against Thurlow Nunn League opposition for the third time this season with the visit of Rayleigh Town to Mayesbrook Park in what will be the first ever game between the teams.

Like Boro, Rayleigh were in FA Vase action at the weekend and like Boro they progressed to the First Round as they beat AFC Pegasus (formerly Stanway Pegasus) 6-5 on penalties after the game at Coggeshall Town’s ground had finished level at 2-2 after 90 minutes.

Rayleigh Town: A Brief History

Rayleigh Town Football Club were founded in 1897 initially under the name Rayleigh Star, changing their name to Rayleigh Town in 1946.

After playing in the Southend & District League, the club joined the Essex Olympian League in 1976, winning the league title in 1979-80, 1980-81, 1983-84 and 1984-85. Further titles were won in 1989-90 and 2000-01 before the club began a groundshare at Concord Rangers that allowed them to step up to the Thurlow Nunn League Division One South for the 2024-25 season.

Rayleigh’s first season at Step 6 ended with them finishing in fourth place and qualifying for the Play-Offs, but after beating AS London 4-1 in the Semi-Final, they lost 2-0 to Hackney Wick in the Final. Rayleigh once again finished fourth in 2025-26, but missed out on promotion for a second time, as after beating Coggeshall Town 3-2 in the Semi-Final, they lost 4-2 at Clapton Community in the Final.

After sharing at Concord Rangers, Rayleigh are this season playing home games at Bowers & Pitsea, but are hopeful of a return to Rayleigh in the future.

This Season:

Rayleigh are currently 13th in the Thurlow Nunn League Division One South, one place below Burnham Ramblers, whom Boro played on Saturday, and have 10 points from the seven league games they have played to date.

They began the season with a 2-2 draw at home to Marcelona, but followed this up with a 5-2 defeat away to FC Baresi before gaining their first win when they beat London Fennecs 3-1. Results since have been mixed with wins over London Harts United and Lymore Gardens balanced with defeats at home to Hertford Heath (4-1) and against Coggeshall Town (also at home, 6-2).

Rayleigh received a bye in the First Qualifying Round of the FA Vase before beating AFC Pegasus in the Second Qualifying Round on Saturday.

BBC Essex Senior Cup:

Should tomorrow night’s game finish level after 90 minutes, no extra-time will be played, and a penalty shoot-out will determine the winners, as was the case in Boro’s First Round tie in this competition. In that game, goalkeeper George Sapsford saved three penalties on his debut as Boro won 3-1 after the 90 minutes against Harwich & Parkeston had finished goal-less. Rayleigh progressed through the First Round with a 4-1 away win against AFC Pegasus.

George Sapsford is congratulated by his team-mates after the penalty shoot-out against Harwich & Parkeston. Photo: Bob Knightley

First Round results:

West Essex v Halstead Town 0-3
Clacton Town v Heybridge Swifts 1-2
Dunmow Town v Lymore Gardens 3-2
Clapton Community v Wivenhoe Town 1-3
Burnham Ramblers v Hutton 3-4
Basildon United v Stansted 2-2 (Stansted won 5-3 on penalties)
Romford v Harwich & Parkeston 0-0 (Romford won 3-1 on penalties)
Frenford v Saffron Walden Town 5-2
Hullbridge Sports v Holland 5-0
East Thurrock Community v Harlow Town 3-1
Ilford v Cannons Wood 2-5
AFC Pegasus Colchester v Rayleigh Town 1-4
Hackney Wick v Great Wakering Rovers 2-3
Benfleet v Southend Manor 2-2 (Southend Manor won 5-4 on penalties)
Basildon Town v Buckhurst Hill 1-0
Marcelona v Little Oakley 1-4
May & Baker EC v Coggeshall Town 3-3 (Coggeshall Town won 4-2 on penalties)
White Ensign v Barking 2-1

Second Round fixtures:

Tuesday 15th September:
Little Oakley v Frenford
Heybridge Swifts v Halstead Town
Romford v Rayleigh Town
East Thurrock Community v Hutton
Southend Manor v Hullbridge Sports
Stansted v Basildon Town

Wednesday 16th September:
Coggeshall Town v Wivenhoe Town
White Ensign v Cannons Wood
Dunmow Town v Great Wakering Rovers