Scottish League Challenge Cup 1999/2000
| Scottish League Challenge Cup | |
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| Association | Scottish FA |
| First edition | 1990/91 |
| Teams | 30th |
| Game mode | Knockout system |
| Title holder | Alloa Athletic (1st title) |
| Record winner |
FC Falkirk Hamilton Academical (2 wins each) |
| Website | scottishfootballleague.com |
The Scottish League Challenge Cup was played for the 9th time in 1999/2000 . The Scottish football competition, officially known as Bell's Challenge Cup was held, began on 10 August 1999 and ended with the final on 21 November 1999 at the Excelsior Stadium of Airdrie . Defending champion FC Falkirk dropped out of the competition in this year's first round against FC Stranraer . This year Alloa Athletic won the tournament in the final against Inverness Caledonian Thistle on penalties . The clubs of the Scottish Football League took part in the competition.
1 round
The matches took place on August 10, 1999.
| Home team | Visiting team | Result | |
|---|---|---|---|
| Airdrieonians FC | - | Dumbarton FC | 2: 1 |
| FC Arbroath | - | East Fife FC | 3: 2 |
| Ayr United | - | Raith Rovers | 0: 1 |
| Berwick Rangers | - | Queen of the South | 4: 1 |
| Brechin City | - | FC Queen's Park | 0: 1 |
| Clyde FC | - | Ross County | 0: 4 |
| Cowdenbeath FC | - | Alloa Athletic | 0: 4 |
| Dunfermline Athletic | - | Greenock Morton | 2: 2 * |
| East Stirlingshire FC | - | Clydebank FC | 1: 2 a.d. |
| Inverness CT | - | FC St. Mirren | 1-0 |
| Montrose FC | - | Hamilton Academical | 1: 3 |
| Partick Thistle | - | Albion Rovers | 0: 2 |
| Stirling Albion | - | FC Stenhousemuir | 2: 2 ** |
| FC Stranraer | - | Partick Thistle | 2: 2 *** |
* Greenock Morton won on penalties .
** Stirling Albion won on penalties.
*** FC Stranraer won on penalties.
2nd round
The matches took place on August 24, 1999.
| Home team | Visiting team | Result | |
|---|---|---|---|
| Airdrieonians FC | - | Alloa Athletic | 1: 2 |
| Clydebank FC | - | Forfar Athletic | 4: 3 |
| Hamilton Academical | - | Inverness CT | 0: 3 |
| Livingston FC | - | Berwick Rangers | 2: 1 a.d. |
| FC Queen's Park | - | Albion Rovers | 3: 1 |
| Ross County | - | Greenock Morton | 3-0 |
| Stirling Albion | - | FC Arbroath | 1: 1 * |
| FC Stranraer | - | Raith Rovers | 1: 2 |
* Stirling Albion won on penalties .
Quarter finals
The matches took place on September 14, 1999.
| Home team | Visiting team | Result | |
|---|---|---|---|
| Inverness CT | - | Clydebank FC | 2-0 |
| Livingston FC | - | Raith Rovers | 3: 1 |
| Ross County | - | Alloa Athletic | 1: 2 a.d. |
| Stirling Albion | - | FC Queen's Park | 4-0 |
Semifinals
The matches took place on September 28, 1999.
| Home team | Visiting team | Result | |
|---|---|---|---|
| Inverness CT | - | Livingston FC | 1-0 |
| Stirling Albion | - | Alloa Athletic | 1: 2 |
final
| Inverness Caledonian Thistle | Alloa Athletic | ||||||||
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Les Fridge - Ross Tokely , Richard Hastings , Stuart Golabek (72nd Kevin Byers ), Mike Teasdale , Mark McCulloch - Paul Sheerin , Barry Wilson , Charlie Christie - Dennis Wyness (106th Martin Glancy ), Davide Xausa (104th Martin Bavidge ) Coach: Steve Paterson ( Scotland ) |
Mark Cairns - Craig Valentine , Paul McAneny , David Beaton - Jimmy Boyle , Derek Clark , Ian Little , Willie Irvine , Gary Clark (67th Max Christie ), Mark Wilson (65th Gregor McKechnie ) - Martin Cameron Trainer: Terry Christie ( Scotland ) |
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 1: 1 Barry Wilson (28th) 2: 2 Paul Sheerin (46th penalty) 3: 3 Paul Sheerin (56th) 4: 4 Paul Sheerin (112th)
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0-1 Gary Clark (19th) 1-2 Mark Wilson (33rd) 2-3 Martin Cameron (47th) 3-4 Martin Cameron (104th)
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 David Beaton, Ian Little
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