2020–21 Southend United F.C. season
Southend United 2020–21 football season
| 2020–21 season | |||
|---|---|---|---|
| Chairman | Ron Martin | ||
| Manager | Mark Molesley (until 9 April)[1] Phil Brown (since 9 April)[1] | ||
| Stadium | Roots Hall | ||
| League Two | 23rd (relegated) | ||
| FA Cup | First round | ||
| EFL Cup | First round | ||
| EFL Trophy | Group stage | ||
| Top goalscorer | League: Tom Clifford Timothée Dieng (3 goals) All: Tom Clifford Timothée Dieng James Olayinka (3 goals) | ||
| |||
The 2020–21 Southend United F.C. season is the club's 115th season in their history and the first season in EFL League Two following their relegation. Along with League Two, the club will also participate in the FA Cup, EFL Cup and EFL Trophy.
The season covers the period from 1 July 2020 to 30 June 2021.
Transfers
Transfers in
| Date | Position | Nationality | Name | From | Fee | Ref. |
|---|---|---|---|---|---|---|
| 5 September 2020 | CB |  | Shaun Hobson | AFC Bournemouth | Free transfer | [2] |
| 17 September 2020 | CF |  | Simeon Akinola | Barnet | Free transfer | [3] |
| 17 September 2020 | DM |  | Alan McCormack | Northampton Town | Free transfer | [4] |
| 5 October 2020 | LM | | Ashley Nathaniel-George | Crawley Town | Undisclosed | [5] |
| 11 November 2020 | LB | | Sam Hart | Blackburn Rovers | Free transfer | [6] |
| 15 December 2020 | CB | | Greg Halford |  Free agent | — | [7] |
| 26 December 2020 | MF | | Louis Walsh | Nottingham Forest | Free transfer | [8] |
| 28 January 2021 | CM | | Nathan Ferguson | Crawley Town | Undisclosed | [9] |
| 1 February 2021 | CM | | Jacob Mellis | Gillingham | Undisclosed | [10] |
| 18 February 2021 | LW | | Ricky Holmes | Northampton Town | Free transfer | [11] |
| 18 February 2021 | CF | | Nile Ranger | Spalding United | Free transfer | [12] |
Loans in
| Date from | Position | Nationality | Name | From | Date until | Ref. |
|---|---|---|---|---|---|---|
| 20 August 2020 | RW | | Jordan Green | Barnsley | 8 October 2020[a] | [13][14] |
| 25 September 2020 | CM | | Kyle Taylor | AFC Bournemouth | 1 January 2021 | [15] |
| 9 October 2020 | CF | | Kazaiah Sterling | Tottenham Hotspur | 4 January 2021 | [16] |
| 17 October 2020 | CM | | James Olayinka | Arsenal | 27 January 2021 | [17] |
| 7 January 2021 | CF | | Reeco Hackett-Fairchild | Portsmouth | End of season | [18] |
| 25 January 2021 | CB | | Tyler Cordner | Bournemouth | End of season | [19] |
| 27 February 2021 | GK | | Alex Bass | Portsmouth | 6 March 2021 | [20] |
| 2 March 2021 | GK | | James Montgomery | Gateshead | 16 March 2021 | [21][22] |
- ^ Loan cut short due to an ankle injury.
Loans out
| Date from | Position | Nationality | Name | To | Date until | Ref. |
|---|---|---|---|---|---|---|
| 23 October 2020 | CB |  | Harry Kyprianou | Bromley | 2 January 2021 | [23] |
| 26 February 2021 | CB | | Richard Taylor | Barnet | End of season | [24] |
Transfers out
| Date | Position | Nationality | Name | To | Fee | Ref. |
|---|---|---|---|---|---|---|
| 1 July 2020 | MF | | Henry Burnett | Crawley Town | Released | [25][26] |
| 1 July 2020 | CM | | Luke Hyam | Unattached | Released | [25] |
| 1 July 2020 | CM | | Sam Mantom | Rushall Olympic | Released | [25][27] |
| 1 July 2020 | DM |  | Mark Milligan | Macarthur | Released | [25][28] |
| 1 July 2020 | CF |  | Theo Robinson | Port Vale | Released | [25][29] |
| 2 July 2020 | CB | | Joe Shaughnessy |  St Mirren | Released | [30][31] |
| 22 August 2020 | LM | | Sam Barratt | Maidenhead United | Released | [32][33] |
| 26 August 2020 | LM | | Stephen McLaughlin | Mansfield Town | Rejected contract | [34][35] |
| 11 September 2020 | CF | | Stephen Humphrys | Rochdale | Undisclosed | [36] |
| 2 October 2020 | LW | | Isaac Hutchinson | Derby County | Undisclosed | [37] |
| 14 October 2020 | CF |  | Charlie Kelman | Queens Park Rangers | Undisclosed | [38] |
Pre-season
Southend United v Millwall
| 29 August 2020 Friendly | Southend United | 0–3 | Millwall | Southend-on-Sea |
| 14:00 BST | Report | Leonard  6'Thompson 35'Parrott 57' | Stadium: Roots Hall Attendance: 0 |
Competitions
EFL League Two
League table
| Pos | Team
| Pld | W | D | L | GF | GA | GD | Pts | Promotion, qualification or relegation |
|---|---|---|---|---|---|---|---|---|---|---|
| 17 | Harrogate Town | 46 | 16 | 9 | 21 | 52 | 61 | −9 | 57 | |
| 18 | Oldham Athletic | 46 | 15 | 9 | 22 | 72 | 81 | −9 | 54 | |
| 19 | Walsall | 46 | 11 | 20 | 15 | 45 | 53 | −8 | 53 | |
| 20 | Colchester United | 46 | 11 | 18 | 17 | 44 | 61 | −17 | 51 | |
| 21 | Barrow | 46 | 13 | 11 | 22 | 53 | 59 | −6 | 50 | |
| 22 | Scunthorpe United | 46 | 13 | 9 | 24 | 41 | 64 | −23 | 48 | |
| 23 | Southend United (R) | 46 | 10 | 15 | 21 | 29 | 58 | −29 | 45 | Relegation to National League |
| 24 | Grimsby Town (R) | 46 | 10 | 13 | 23 | 37 | 69 | −32 | 43 |
Updated to match(es) played on 31 May 2021. Source: EFL Official Website
Rules for classification: 1) Points; 2) Goal difference; 3) Number of goals scored; 4) Head-to-head results; 5) Wins; 6) Away goals; 7) Penalty points (sec 9.5); 8) 12-point sending off offences[39]
(R) Relegated
Rules for classification: 1) Points; 2) Goal difference; 3) Number of goals scored; 4) Head-to-head results; 5) Wins; 6) Away goals; 7) Penalty points (sec 9.5); 8) 12-point sending off offences[39]
(R) Relegated
Results summary
| Overall | Home | Away | |||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Pld | W | D | L | GF | GA | GD | Pts | W | D | L | GF | GA | GD | W | D | L | GF | GA | GD |
| 46 | 10 | 15 | 21 | 29 | 60 | −31 | 45 | 5 | 6 | 12 | 17 | 30 | −13 | 5 | 9 | 9 | 12 | 30 | −18 |
Last updated: 8 May 2021.
Source: BBC
Results by matchday
Updated to match(es) played on 8 May 2021. Source: 11v11 for league tables and fixtures
A = Away; H = Home; W = Win; D = Draw; L = Loss
A = Away; H = Home; W = Win; D = Draw; L = Loss
Matches
Win Draw Loss Postponed
The 2020/21 season fixtures were released on 21 August.[40]
Southend United v Harrogate Town
| 12 September 2020 1 | Southend United | 0–4 | Harrogate Town | Southend-on-Sea |
| 15:00 BST | Taylor  7'Hutchinson 90+3' | Report | Muldoon 25', 69' Kerry 44'Martin 46' 60' | Stadium: Roots Hall Attendance: 0 Referee: Antony Coggins |
Carlisle United v Southend United
| 19 September 2020 2 | Carlisle United | 2–0 | Southend United | Carlisle |
| 13:00 BST | Anderton 16' Patrick 36'Kayode 39' | Report | Stadium: Brunton Park Attendance: 1,000 Referee: Graham Salisbury |
Southend United v Morecambe
| 26 September 2020 3 | Southend United | 1–2 | Morecambe | Southend-on-Sea |
| 15:00 BST | Gibson 5' (o.g.) Taylor 15'Demetriou 37' | Report | Phillips 33' 73' Kenyon 37'Wildig 55' | Stadium: Roots Hall Attendance: 0 Referee: Charles Breakspear |
Crawley Town v Southend United
| 3 October 2020 4 | Crawley Town | 1–1 | Southend United | Crawley |
| 15:00 BST | Nadesan 21' Craig 90+4' | Report | Ralph 84' | Stadium: The People's Pension Stadium Attendance: 0 Referee: Brett Huxtable |
Southend United v Exeter City
| 10 October 2020 5 | Southend United | 2–2 | Exeter City | Southend-on-Sea |
| 15:00 BST | Goodship 26' Demetriou 65' (pen.) | Report | Randall 40' Fisher 90+5' | Stadium: Roots Hall Attendance: 0 Referee: Kevin Johnson |
Southend United v Cheltenham Town
| 17 October 2020 6 | Southend United | 0–2 | Cheltenham Town | Southend-on-Sea |
| 15:00 BST | Demetriou 67' | Report | Sercombe 10' (pen.) Lloyd 52' | Stadium: Roots Hall Attendance: 0 Referee: James Oldham |
Salford City v Southend United
| 20 October 2020 7 | Salford City | 3–0 | Southend United | Salford |
| 19:45 BST | Lennon 26' (o.g.) Clarke 50'Wilson 58'Henderson 63'Thomas-Asante 71' | Report | Olayinka 27' Dieng 43'Lennon 45+1'Taylor 81'Demetriou 90+1' | Stadium: Moor Lane Attendance: 0 Referee: Carl Boyeson |
Tranmere Rovers v Southend United
| 24 October 2020 8 | Tranmere Rovers | 2–0 | Southend United | Birkenhead |
| 15:00 BST | Clarke 31' Vaughan 52' 83' | Report | Stadium: Prenton Park Attendance: 0 Referee: Andy Woolmer |
Southend United v Oldham Athletic
| 27 October 2020 9 | Southend United | 1–2 | Oldham Athletic | Southend-on-Sea |
| 19:00 GMT | Clifford 76' | Report | Grant 49' Piergianni 74'Dearnley 89'Clarke 90+4' | Stadium: Roots Hall Attendance: 0 Referee: Chris Sarginson |
Southend United v Port Vale
| 31 October 2020 10 | Southend United | 0–2 | Port Vale | Southend-on-Sea |
| 15:00 GMT | Lennon 85' | Report | Legge 22' Pope 48', 64'Clark 83' | Stadium: Roots Hall Attendance: 0 Referee: Tom Nield |
Bradford City v Southend United
| 3 November 2020 11 | Bradford City | 3–0 | Southend United | Bradford |
| 19:00 GMT | Cooke 5' Watt 33'Pritchard 43' 80'Donaldson 77' | Report | Demetriou 43' Acquah 54'Dieng 90' | Stadium: Utilita Energy Stadium Attendance: 0 Referee: Marc Edwards |
Walsall v Southend United
| 14 November 2020 12 | Walsall | 0–1 | Southend United | Bescot |
| 15:00 GMT | Bates 83'  90+3' | Report | Lennon 43' Acquah 88' | Stadium: Banks's Stadium Attendance: 0 Referee: Craig Hicks |
Southend United v Forest Green Rovers
| 24 November 2020 13 | Southend United | 0–1 | Forest Green Rovers | Southend-on-Sea |
| 19:00 GMT | Dieng 62' McCormack 88' | Report | Young 63' | Stadium: Roots Hall Attendance: 0 Referee: Keith Stroud |
Bolton Wanderers v Southend United
| 28 November 2020 (2020-11-28) 14 | Bolton Wanderers | 3–0 | Southend United | Bolton |
| 15:00 BST | Delfouneso 45+1' Sarcevic 53'Doyle 65' (pen.), 81'White 79' | Report | Stadium: University of Bolton Stadium Attendance: 0 Referee: John Busby |
Stevenage v Southend United
| 5 December 2020 15 | Stevenage | 0–0 | Southend United | Stevenage |
| 15:00 GMT | Newton 57' | Report | Taylor 68' Olayinka 74' | Stadium: Lamex Stadium Attendance: 0 Referee: Declan Bourne |
Southend United v Scunthorpe United
| 12 December 2020 16 | Southend United | 1–0 | Scunthorpe United | Southend-on-Sea |
| 15:00 GMT | Olayinka 80' | Report | Stadium: Roots Hall Attendance: 2,000 Referee: Stephen Martin |
Southend United v Grimsby Town
| 15 December 2020 17 | Southend United | 3–1 | Grimsby Town | Southend-on-Sea |
| 19:45 GMT | Taylor 1' Clifford 57'Halford 75'Egbri 89' | Report | Jackson Jr 45+4' Hewitt 68'Waterfall 73' 90+4' | Stadium: Roots Hall Attendance: 0 Referee: Sam Allison |
Mansfield Town v Southend United
| 19 December 2020 18 | Mansfield Town | 1–1 | Southend United | Mansfield |
| 15:00 GMT | Clarke 56' Cook 77'Bowery 79' | Report | Olayinka 27' Egbri 65'Klass 72'Taylor 78' | Stadium: One Call Stadium Attendance: 0 Referee: Brett Huxtable |
Southend United v Colchester United
| 26 December 2020 19 | Southend United | 2–0 | Colchester United | Southend-on-Sea |
| 13:00 GMT | Akinola 10' Hart 17'Dieng 22'Hobson 90+6' | Report | Eastman 43' Senior 59'Chilvers 90+6'Lapslie 90+6' | Stadium: Roots Hall Attendance: 0 Referee: Neil Hair |
Leyton Orient v Southend United
| 29 December 2020 20 | Leyton Orient | 2–0 | Southend United | Leyton |
| 19:00 GMT | McAnuff 53' Wilkinson 78'Angol 90'Johnson 90+1' | Report | Dieng 52' Bwomono 53' | Stadium: Breyer Group Stadium Attendance: 0 Referee: Craig Hicks |
Southend United v Barrow
| 9 January 2021 21 | Southend United | 1–0 | Barrow | Southend-on-Sea |
| 15:00 GMT | Hackett-Fairchild 3' Halford 17' 52'Oxley 79' | Report | Hird 54' Kay 83' | Stadium: Roots Hall Attendance: 0 Referee: Christopher Pollard |
Grimsby Town v Southend United
| 16 January 2021 22 | Grimsby Town | 0–0 | Southend United | Cleethorpes |
| 15:00 GMT | Habergham 71' Spokes 90+1' | Report | McCormack 74' White 75'Demetriou 90+4' | Stadium: Blundell Park Attendance: 0 Referee: Ben Toner |
Southend United v Cambridge United
| 19 January 2021 23 | Southend United | 1–2 | Cambridge United | Southend-on-Sea |
| 19:00 GMT | Akinola 27' Hart 40'Oxley 90+6' | Report | Digby 40' Iredale 46'Ironside 68' | Stadium: Roots Hall Attendance: 0 Referee: Bobby Madley |
Southend United v Mansfield Town
| 23 January 2021 24 | Southend United | 0–1 | Mansfield Town | Southend-on-Sea |
| 15:00 GMT | Dieng 54' 84' Hart 78' | Report | Reid 64' Quinn 70' | Stadium: Roots Hall Attendance: 0 Referee: Ben Speedie |
Southend United v Bradford City
| 26 January 2021 25 | Southend United | 1–3 | Bradford City | Southend-on-Sea |
| 19:00 GMT | Bwomono 31' Cordner 37' | Report | Evans 23', 74' Rowe 57' | Stadium: Roots Hall Attendance: 0 Referee: Trevor Kettle |
Port Vale v Southend United
| 30 January 2021 26 | Port Vale | 5–1 | Southend United | Burslem |
| 15:00 GMT | Rodney 1', 45+2' Cordner 20' (o.g.)Crookes 27'Oyeleke 89' | Report | Demetriou 23' Nathaniel-George 67'Ferguson 85'Hobson 90+3' | Stadium: Vale Park Attendance: 0 Referee: Carl Brook |
Newport County v Southend United
| 9 February 2021 27 | Newport County | 0–1 | Southend United | Newport |
| 19:00 GMT | Report | Clifford 74' | Stadium: Rodney Parade Attendance: 0 Referee: Paul Howard |
Cambridge United v Southend United
| 13 February 2021 28 | Cambridge United | 0–0 | Southend United | Cambridge |
| 15:00 GMT | May 41' Okedina 85' | Stadium: Abbey Stadium Attendance: 0 Referee: Ross Joyce |
Southend United v Bolton Wanderers
| 20 February 2021 29 | Southend United | 0–1 | Bolton Wanderers | Southend-on-Sea |
| 15:00 GMT | Ferguson 32' Bwomono 83' | Report | Williams 75' Miller 82'John 85' | Stadium: Roots Hall Attendance: 0 Referee: Declan Bourne |
Forest Green Rovers v Southend United
| 24 February 2021 30 | Forest Green Rovers | 1–3 | Southend United | Nailsworth |
| 18:00 GMT | Moore-Taylor 35' Wagstaff 82'Matt 86' | Report | Hobson 20', 51' Dieng 55'Bwomono 67'Ferguson 70' | Stadium: The Innocent [Insert Name Here] Stadium Attendance: 0 Referee: Lee Swabey |
Southend United v Salford City
| 27 February 2021 31 | Southend United | 0–0 | Salford City | Southend-on-Sea |
| 15:00 GMT | Hackett-Fairchild 14' McCormack 79' | Report | Gotts 61' | Stadium: Roots Hall Attendance: 0 Referee: Dean Whitestone |
Cheltenham Town v Southend United
| 2 March 2021 32 | Cheltenham Town | 1–0 | Southend United | Cheltenham |
| 19:00 GMT | Thomas 53' (pen.) | Report | Stadium: Whaddon Road Ground Attendance: 0 Referee: Will Finnie |
Oldham Athletic v Southend United
| 6 March 2021 33 | Oldham Athletic | 0–0 | Southend United | Oldham |
| 15:00 GMT | Report | Demetriou 88' | Stadium: Boundary Park Attendance: 0 Referee: Ollie Yates |
Southend United v Tranmere Rovers
| 9 March 2021 34 | Southend United | 0–2 | Tranmere Rovers | Southend-on-Sea |
| 19:00 GMT | White 55' Hackett-Fairchild 86' | Report | Lewis 8' Ray 24' | Stadium: Roots Hall Attendance: 0 Referee: Tim Robinson |
Southend United v Stevenage
| 13 March 2021 35 | Southend United | 0–0 | Stevenage | Southend-on-Sea |
| 15:00 GMT | McCormack 66' Demetriou 77'Hackett-Fairchild 81' | Report | Prosser 45+4' | Stadium: Roots Hall Attendance: 0 Referee: Peter Wright |
Scunthorpe United v Southend United
| 20 March 2021 36 | Scunthorpe United | 1–1 | Southend United | Scunthorpe |
| 15:00 GMT | Karacan 75' Clarke  78'Beestin 90' | Report | Hart 62' Dieng 67'Nathaniel-George 79' (pen.) | Stadium: Sands Venue Stadium Attendance: 0 Referee: Robert Lewis |
Southend United v Walsall
| 23 March 2021 37 | Southend United | 0–0 | Walsall | Southend-on-Sea |
| 19:00 GMT | McCormack 4' White 36'Hart 67' | Report | Gordon 31' Lavery 36'Clarke 82'Leak 83'Osei 90' | Stadium: Roots Hall Attendance: 0 Referee: David Rock |
Harrogate Town v Southend United
| 27 March 2021 38 | Harrogate Town | 0–1 | Southend United | Harrogate |
| 15:00 GMT | Hall 87' | Report | Demetriou 44' Hobson 67'Nathaniel-George 69', 90+2' | Stadium: The EnviroVent Stadium Attendance: 0 Referee: Leigh Doughty |
Southend United v Carlisle United
| 3 April 2021 39 | Southend United | 0–2 | Carlisle United | Southend-on-Sea |
| 13:00 BST | Akinola  38'Taylor 38' | Report | Zanzala 17' McDonald 31'Touré 79' | Stadium: Roots Hall Attendance: 0 Referee: Alan Young |
Morecambe v Southend United
| 6 April 2021 40 | Morecambe | 1–1 | Southend United | Morecambe |
| 18:30 BST | Stockton 56' | Report | Dieng 18' Dimitriou 68' | Stadium: Mazuma Stadium Attendance: 0 Referee: Scott Oldham |
Southend United v Crawley Town
| 10 April 2021 41 | Southend United | 0–0 | Crawley Town | Southend-on-Sea |
| 15:00 BST | Halford 49' Demetriou 70'Clifford 76' | Report | Stadium: Roots Hall Attendance: 0 Referee: Charles Breakspear |
Exeter City v Southend United
| 17 April 2021 42 | Exeter City | 0–0 | Southend United | Exeter |
| 12:30 BST | Page 45' Willmott 74' | Report | Walsh 38' | Stadium: St James Park Attendance: 0 Referee: Darren Drysdale |
Colchester United v Southend United
| 20 April 2021 43 | Colchester United | 2–0 | Southend United | Colchester |
| 19:00 BST | Folivi 30' Pell 37'Harriott 49' | Report | Demetriou 69' White 75'Cordner 90+1'Halford 90+3' | Stadium: JobServe Community Stadium Attendance: 0 Referee: Kevin Johnson |
Southend United v Leyton Orient
| 24 April 2021 44 | Southend United | 2–1 | Leyton Orient | Southend-on-Sea |
| 15:00 BST | Cordner 42', 83' Rush 76'Hart 80'Walsh 82' | Report | Dennis 45+3' | Stadium: Roots Hall Attendance: 0 Referee: Trevor Kettle |
Barrow v Southend United
| 1 May 2021 45 | Barrow | 1–2 | Southend United | Barrow-in-Furness |
| 15:00 BST | Quigley 19' Kay 29'Thomas 61'Ntlhe 65'Andrew 79'Brown 90+5' | Report | White 30' Cordner 40'Hart 45'Egbri 52' | Stadium: Furness Building Society Stadium Attendance: 0 Referee: Martin Coy |
Southend United v Newport County
| 8 May 2021 46 | Southend United | 1–1 | Newport County | Southend-on-Sea |
| 15:00 BST | Hobson 11', 51' Halford 41'Rush 61' | Report | Demetriou 56' | Stadium: Roots Hall Attendance: 0 Referee: John Brooks |
FA Cup
The draw for the first round was made on Monday 26, October.[41]
Win Draw Loss
Boreham Wood v Southend United
| 8 November 2020 First round | Boreham Wood | 3–3 (a.e.t.) (4–3 p) | Southend United | Borehamwood |
| 15:00 GMT | Fyfield 8' Ricketts 51'Ilesanmi 53'Rhead 73'Mafuta 76'Tshimanga 93' (pen.)Ashmore 96'Thomas 104' | Report | Goodship 59' Egbri 63'Olayinka 100' | Stadium: Meadow Park Attendance: 0 Referee: Ben Toner |
| Penalties | ||||
| Coulthirst Mingoia  Thomas Tshimanga Mafuta | Olayinka Clifford Rush Nathaniel-George Demetriou | |||
EFL Cup
Win Draw Loss
The first round draw was made on 18 August, live on Sky Sports, by Paul Merson.[42]
Gillingham v Southend United
| 5 September 2020 First round | Gillingham | 1–0 | Southend United | Gillingham |
| 13:00 BST | Ogilvie 27' Jackson 40' 58'O'Keefe 60' | Report | Hobson 25' White 47'Hutchinson 56' | Stadium: Priestfield Stadium Attendance: 0 Referee: Christopher Pollard |
EFL Trophy
Win Draw Loss
The regional group stage draw was confirmed on 18 August.[43]
| Pos | Div | Team
| Pld | W | PW | PL | L | GF | GA | GD | Pts | Qualification |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | ACA | West Ham United U21 | 3 | 3 | 0 | 0 | 0 | 5 | 1 | +4 | 9 | Advance to Round 2 |
| 2 | L1 | Portsmouth | 3 | 2 | 0 | 0 | 1 | 5 | 1 | +4 | 6 | |
| 3 | L2 | Colchester United | 3 | 1 | 0 | 0 | 2 | 6 | 4 | +2 | 3 | |
| 4 | L2 | Southend United | 3 | 0 | 0 | 0 | 3 | 2 | 12 | −10 | 0 |
Source: EFL.com
Southend United v West Ham United U21
| 8 September 2020 Group stage | Southend United | 1–3 | West Ham United U21 | Southend-on-Sea |
| 17300 BST | Humphrys 13' 35' | Report | Odubeko 2', 84' Ashby 63'Costa Da Rose 71'Coventry 90+1' | Stadium: Roots Hall Attendance: 0 Referee: David Rock |
Southend United v Portsmouth
| 6 October 2020 Group stage | Southend United | 0–3 | Portsmouth | Southend-on-Sea |
| 19:45 BST | Rush 35' Coker 59'Taylor 84' | Report | Marquis 21' (pen.) Curtis 40', 77'Bolton 78' | Stadium: Roots Hall Attendance: 0 Referee: Paul Howard |
Colchester United v Southend United
| 10 November 2020 Group stage | Colchester United | 6–1 | Southend United | Colchester |
| 19:00 GMT | Brown 16', 38', 57' (pen.) Folivi 62'Marshall-Miranda 67'Chilvers 70'Poku 83' | Report | White 39' Egbri 54'Chandler 61'Hobson 90'Sterling 90+2' | Stadium: JobServe Community Stadium Attendance: 0 Referee: Alan Young |
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