| 1999–2000 Bell's Challenge Cup | |
| Country: | Scotland |
| Num Teams: | 30 |
| Defending Champions: | Falkirk |
| Champions: | Alloa Athletic |
| Runner-Up: | Inverness Caledonian Thistle |
| Matches: | 29 |
| Goals: | 98 |
| Prevseason: | 1997–98 |
| Nextseason: | 2000–01 |
The 1999–2000 Scottish Challenge Cup was the ninth season of the competition, which was also known as the Bell's Challenge Cup for sponsorship reasons. It was competed for by the 30 member clubs of the Scottish Football League. The defending champions were Falkirk, who defeated Queen of the South 1–0 in the 1997 final.[1]
The final was played on 21 November 1999,[2] between Inverness Caledonian Thistle and Alloa Athletic at Excelsior Stadium in Airdrie. Alloa Athletic won 5–4 on penalties after a 4–4 draw after extra time,[2] to win the tournament for the first time in the club's history.
| Round | First match date | Fixtures | width=100 | Clubs | ||
|---|---|---|---|---|---|---|
| align=left | First round | align=left | Tuesday 10 August 1999 | 14 | 30 → 16 | |
| align=left | Second round | align=left | Tuesday 24 August 1999 | 8 | 16 → 8 | |
| align=left | Quarter-finals | align=left | Tuesday 14 September 1999 | 4 | 8 → 4 | |
| align=left | Semi-finals | align=left | Tuesday 28 September 1999 | 2 | 4 → 2 | |
| align=left | align=left | Sunday 21 November 1999 | 1 | 2 → 1 |
Forfar Athletic and Livingston received random byes into the second round.Source: Soccerbase
Source: Soccerbase
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See main article: 1999 Scottish Challenge Cup Final.
A. The 1998–99 tournament was suspended due to lack of sponsorship