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The 2019–20 Scottish Challenge Cup known as the Tunnock's Caramel Wafer Challenge Cup due to sponsorship reasons, was the 29th season of the competition. The total number of participating clubs is 58. The competition began on 6 August 2019 with the First Round and was due to end on 28 March 2020 with the final at McDiarmid Park in Perth. However, the final had to be postponed due to the COVID-19 pandemic and was never subsequently played.

Thirty teams from the Championship, League One and League Two compete, along with four teams from the Highland Football League and four from the Lowland Football League. In addition to this, Under-21 teams of the clubs competing in the Premiership are represented. This season there will be again two clubs from Northern Ireland's NIFL Premiership, two clubs from the Welsh Premier League, two clubs from the Republic of Ireland's League of Ireland and for the second time two entrants from the English National League (fifth tier) entered into the competition.

Ross County were the cup holders after they beat Connah's Quay 3–1 in the 2019 final, but they were ineligible to defend their title following their promotion to the Premiership for the 2019–20 season.

Format

First round

The first round featured 4 clubs from the 2018-19 Scottish Highland Football League (Cove Rangers, Brora Rangers, Fraserburgh, Formartine United), 4 clubs from the 2018-19 Scottish Lowland Football League (East Kilbride, BSC Glasgow, Kelty Hearts, Spartans), 4 clubs from 2018–19 Ladbrokes League Two (Queen's Park, Elgin City, Albion Rovers, Berwick Rangers) and the 12 Under 21 teams of the 2019-20 Scottish Premiership.

The draw was made on 26 June 2019 at 12:30 in the Tunnock's factory in Uddingston and was broadcast live on the SPFL YouTube Channel. The draw was regionalised and all non-Under 21 teams were seeded. The matches were played on 6 and 7 August 2019.

North Section

Draw

Teams in bold advanced to the second round.

Matches

6 August 2019	Livingston U21s	1–3	Formartine United	Livingston, Scotland
19:45	Henderson 90+4' (pen.)		McGowan 9' Gethins 19' Wood 84'	Stadium: Almondvale Stadium Attendance: 120 Referee: Jordan Curran

6 August 2019	Albion Rovers	1–4	Heart of Midlothian U21s	Coatbridge, Scotland
19:45	Osadolor 34'		Petkov 24' Keena 29', 78' Henderson 75'	Stadium: Cliftonhill Attendance: 207 Referee: Alan Muir

6 August 2019	St Johnstone U21s	1–4	Cove Rangers	Perth, Scotland
19:45	Northcott 2'		Brown 27' Park 79' Megginson 81' Scott 88'	Stadium: McDiarmid Park Attendance: 175 Referee: Matthew MacDermid

South Section

Draw

Teams in bold advanced to the second round.

Matches

6 August 2019	Berwick Rangers	1–2	Rangers U21s	Berwick-upon-Tweed, England
19:45	Purves 71'		Mebude 24' (pen.) McPake 31'	Stadium: Shielfield Park Attendance: 303 Referee: Colin Whyte

6 August 2019	St Mirren U21s	1–0	East Kilbride	Paisley, Scotland
19:45	Breadner 32'			Stadium: St Mirren Park Attendance: 245 Referee: Jordan Paterson

7 August 2019	Motherwell U21s	1–0	Spartans	Airdrie, Scotland
19:45	Semple 18'			Stadium: Excelsior Stadium Attendance: 170 Referee: Ross Hardie

Second round

The draw was also made on 26 June 2019 at 12:30 in the Tunnock's factory in Uddingston and was broadcast live on the SPFL YouTube Channel. The draw was again regionalised but not seeded. Matches were played on 13 August 2019.

North Section

Matches

13 August 2019	Heart of Midlothian U21s	3–1	Cowdenbeath	Linlithgow, Scotland
19:45	Baur 71' Keena 80' Zanatta 82'		Barr 87'	Stadium: Prestonfield Attendance: 326 Referee: Lloyd Wilson

13 August 2019	Brora Rangers	1–2	Cove Rangers	Brora, Scotland
19:45	MacLeod 47'		Scully 72' Robertson 81'	Stadium: Dudgeon Park Attendance: 300 Referee: Gordon Morrison

13 August 2019	Montrose	2–1	Forfar Athletic	Montrose, Scotland
19:45	Milne 38' Lyons 71'		MacKintosh 36'	Stadium: Links Park Attendance: 531 Referee: Gavin Duncan

South Section

Matches

13 August 2019	Annan Athletic	1–1 (5–6 p)	Kelty Hearts	Annan, Scotland
19:45	Currie 20'		Ashe 69'	Stadium: Galabank Attendance: 307 Referee: Peter Stuart
	Penalties
	Muir McLean Wilkie McLear Nadé Bradley Douglas		Ashe Russell Linton Reilly Husband Philp McKirdy

13 August 2019	Hamilton Academical U21s	0–1	Airdrieonians	Hamilton, Scotland
19:45			Carrick 14'	Stadium: New Douglas Park Attendance: 323 Referee: David Lowe

13 August 2019	Dumbarton	0–1	St Mirren U21s	Dumbarton, Scotland
19:45			Jack 30'	Stadium: Dumbarton Football Stadium Attendance: 279 Referee: Craig Napier

13 August 2019	Stenhousemuir	2–1	Edinburgh City	Stenhousemuir, Scotland
19:30	Watters 33', 74'		Henderson 72'	Stadium: Ochilview Park Attendance: 178 Referee: Scott Lambie

13 August 2019	Falkirk	1–1 (6–5 p)	Celtic U21s	Falkirk, Scotland
19:45	Longridge 10'		Robertson 11'	Stadium: Falkirk Stadium Attendance: 1,076 Referee: David Dickinson
	Penalties
	Telfer Sammon Johnstone McShane Longridge Buchanan Connolly		Henderson Welsh Robertson Connell Burt Miller Aitchison

Third round

The 14 winners of the Second Round are joined by the 10 clubs from the Scottish Championship and two teams from the National League, the NIFL Premiership, the Welsh Premier League and the League of Ireland Premier Division.

A pre-draw determined which country was allocated to Pot A, Pot B, Pot C and Pot D to avoid 2 cross-border teams from the same country playing each other. Pot E had the remaining 24 Scottish teams. Games will be played Saturday 7 September or Sunday 8 September 2019.

The draw was made on 14 August 2019 at 12:30 and was broadcast live on the SPFL YouTube Channel.

Teams in bold advanced to the fourth round.

SPFL			Other Scottish	Teams from other countries
Championship	League One	League Two
Alloa Athletic Arbroath Ayr United Dundee Dundee United Dunfermline Athletic Greenock Morton Inverness Caledonian Thistle Partick Thistle Queen of the South	Airdrieonians Clyde Falkirk Montrose Raith Rovers	Cove Rangers Elgin City Stenhousemuir Stirling Albion	Highland League Formartine United Lowland League Kelty Hearts Premiership U21s Heart of Midlothian U21s Rangers U21s St Mirren U21s	National League Solihull Moors Wrexham NIFL Premiership Ballymena United Glenavon Welsh Premier League The New Saints Connah's Quay Nomads League of Ireland Premier Division Bohemians Waterford

Matches

6 September 2019	Waterford	3–1	Heart of Midlothian U21s	Waterford, Republic of Ireland
19:45	Chvedukas 27' Phelan 79' Madika 84'		Watson 72'	Stadium: Waterford Regional Sports Centre Attendance: 300 Referee: Paul Howard

7 September 2019	Airdrieonians	3–2	Bohemians	Airdrie, Scotland
13:00	Gallagher 19', 72' Smith 77'		Allardice 45+1' Wade-Slater 74'	Stadium: Excelsior Stadium Attendance: 730 Referee: Huw Jones

7 September 2019	Stenhousemuir	1–1 (3–1 p)	The New Saints	Stenhousemuir, Scotland
15:00	Anderson 48'		Brobbel 86'	Stadium: Ochilview Park Attendance: 335 Referee: Damien MacGraith
	Penalties
	Munro Gibson Watters Hopkirk		Whitehouse Cieślewicz Marriott Ebbe

7 September 2019	Wrexham	1–1 (6–5 p)	Ayr United	Wrexham, Wales
15:00	Bickerstaff 70'		Roscoe 86'	Stadium: Racecourse Ground Attendance: 1,697 Referee: Steven Gregg
	Penalties
	Rutherford Bickerstaff Barnum-Bobb Tollitt Barton Lawlor		Docherty Moffat Bell Geggan Forrest McCowan

7 September 2019	Kelty Hearts	1–1 (2–4 p)	Solihull Moors	Kelty, Scotland
15:00	Russell 38'		Stenson 72'	Stadium: New Central Park Attendance: 1,146 Referee: Rob Rogers
	Penalties
	Ashe Russell Linton Reilly		Hawkridge Nicholls Hancox Carter

7 September 2019	Formartine United	0–3	Glenavon	Pitmedden, Scotland
15:00			Daniels 13' Marshall 70' McCloskey 83'	Stadium: North Lodge Park Attendance: 470 Referee: Martin Wood

7 September 2019	Inverness Caledonian Thistle	3–1	Greenock Morton	Inverness, Scotland
15:00	Todorov 25' Doran 31' Storey 57'		Sutton 78'	Stadium: Caledonian Stadium Attendance: 1,021 Referee: Willie Collum

7 September 2019	St Mirren U21s	1–0	Stirling Albion	Paisley, Scotland
15:00	MacPherson 80'			Stadium: St Mirren Park Attendance: 450 Referee: Euan Anderson

7 September 2019	Raith Rovers	2–0	Falkirk	Kirkcaldy, Scotland
15:00	Hendry 17' (pen.), 50' (pen.)			Stadium: Stark's Park Attendance: 1,771 Referee: Greg Aitken

7 September 2019	Dunfermline Athletic	1–2	Alloa Athletic	Dunfermline, Scotland
15:00	Kiltie 29'		Thomson 40' Trouten 53'	Stadium: East End Park Attendance: 1,448 Referee: Steven McLean

7 September 2019	Connah's Quay Nomads	1–0	Cove Rangers	Connah's Quay, Wales
17:15	Bakare 75'			Stadium: Deeside Stadium Attendance: 327 Referee: Thomas Clarke

8 September 2019	Dundee	1–2	Elgin City	Dundee, Scotland
15:00	Kerr 18'		Omar 56' Sutherland 58'	Stadium: Dens Park Attendance: 1,619 Referee: Grant Irvine

18 September 2019	Ballymena United	0–1	Rangers U21s	Ballymena, Northern Ireland
19:45			Atakayi 87'	Stadium: Ballymena Showgrounds Attendance: 895 Referee: Simon Lee Evans

Fourth round

The draw was made on 10 September 2019 at 12:30, live on the SPFL YouTube Channel.

Teams in Italics were not known at the time of the draw. Teams in Bold advanced to the quarter-finals.

SPFL	Teams from other countries
Championship Alloa Athletic Arbroath Inverness Caledonian Thistle Partick Thistle League One Airdrieonians Clyde Raith Rovers League Two Elgin City Stenhousemuir Premiership U21s Rangers U21s St Mirren U21s	National League Solihull Moors Wrexham NIFL Premiership Glenavon Welsh Premier League Connah's Quay Nomads League of Ireland Premier Division Waterford

Matches

11 October 2019	Stenhousemuir	3–2	Waterford	Stenhousemuir, Scotland
19:35	McLaughlin 30' Hopkirk 61' McGuigan 90+4'		Fitzgerald 24' O'Connor 74'	Stadium: Ochilview Park Attendance: 440 Referee: Simon Mather

12 October 2019	Raith Rovers	3–1	Glenavon	Kirkcaldy, Scotland
15:00	Bowie 15' Armstrong 32' Allan 90'		Marshall 24'	Stadium: Stark's Park Attendance: 1,301 Referee: Bryn Markham-Jones

12 October 2019	Wrexham	4–1	St Mirren U21s	Wrexham, Wales
15:00	Redmond 46' McIntosh 55' (pen.), 73' Tollitt 89'		Henderson 68'	Stadium: Racecourse Ground Attendance: 1,468 Referee: Raymond Matthews

12 October 2019	Partick Thistle	2–0	Connah's Quay Nomads	Glasgow, Scotland
17:15	De Vita 34' Penrice 77'			Stadium: Firhill Stadium Attendance: 1,380 Referee: Jamie Robinson

29 October 2019	Solihull Moors	3–3 (3–4 p)	Rangers U21s	Solihull, England
19:45	Howe 8' Yussuf 36' Carter 60'		Barjonas 11' Grezda 69', 84'	Stadium: Damson Park Attendance: 1,598 Referee: John McLoughlin
	Penalties
	Hawkridge Hancox Carter McCallum Bigirimana		Barjonas Patterson Grezda Kennedy

Quarter-finals

The draw was made on 16 October 2019 at 13:00, live on the SPFL YouTube Channel.

Teams in Italics were not known at the time of the draw. Teams in Bold advanced to the semi-finals.

SPFL	National League
Championship Inverness Caledonian Thistle Partick Thistle League One Clyde Raith Rovers League Two Elgin City Stenhousemuir Premiership U21s Rangers U21s	Wrexham

Matches

16 November 2019	Stenhousemuir	1–4	Partick Thistle	Stenhousemuir, Scotland
15:00	Hopkirk 68'		Cole 34' Harkins 70' Slater 79' Miller 86'	Stadium: Ochilview Park Attendance: 1,244 Referee: Alan Muir

16 November 2019	Rangers U21s	2–0	Wrexham	Glasgow, Scotland
15:00	Barjonas 35' Young-Coombes 71'			Stadium: Ibrox Stadium Attendance: 5,426 Referee: Shane Andrews

Semi-finals

The draw was made on 20 November 2019 at 12:00 and was broadcast live on the SPFL YouTube Channel.

The fixtures were played from 14 to 16 February 2020.

SPFL
Championship Inverness Caledonian Thistle Partick Thistle League One Raith Rovers Premiership U21s Rangers U21s

Matches

14 February 2020	Partick Thistle	1–2	Raith Rovers	Glasgow, Scotland
19:45	Mansell 83'		Benedictus 31' Hendry 74'	Stadium: Firhill Stadium Attendance: 2,196 Referee: Alan Newlands

16 February 2020	Inverness Caledonian Thistle	2–1	Rangers U21s	Inverness, Scotland
16:10	Keatings 44' Storey 73'		Mebude 6'	Stadium: Caledonian Stadium Attendance: 1,741 Referee: Greg Aitken

• Note: The final was cancelled as a result of the coronavirus situation, both teams were declared joint winners.

Broadcasting rights

The following matches are to be broadcast live on UK television:

Notes

A. The 2020–21 tournament was cancelled due to the Covid-19 pandemic in Scotland.

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External links

• Scottish Challenge Cup at the Scottish Professional Football League

• Scottish Challenge Cup seasons
• 2019–20 Scottish Professional Football League
• 2019–20 in Scottish football cups
• Association football events postponed due to the COVID-19 pandemic
• 2019–20 in English football
• 2019–20 in Welsh football
• 2019–20 in Northern Ireland association football