Inverness Caledonian Thistle F.C. in their sixth season in the Scottish Football League competed in the Scottish First Division, Scottish League Cup, the Scottish Challenge Cup, the Scottish Challenge Cup where they made their first major final against Second Division team Alloa Athletic where they lost on a penalty shoot-out after a 4–4 draw and Scottish Cup where they famously beat Scottish Premier League team Celtic 3–1 in the 3rd Round in season 1999–2000.
| Club: | Inverness Caledonian Thistle F.C. |
| Season: | 1999–2000 |
| Manager: | Steve Paterson |
| Mgrtitle: | Manager |
| Chrtitle: | Chairman |
| League: | Scottish First Division |
| League Result: | 6th |
| Cup1: | Scottish Cup |
| Cup1 Result: | 4th Round |
| Cup2: | Scottish League Cup |
| Cup2 Result: | 3rd Round |
| Cup3: | Scottish Challenge Cup |
| Cup3 Result: | Finalists |
| League Topscorer: | Barry Wilson (13) |
| Season Topscorer: | Paul Sheerin (17) |
| Highest Attendance: | 6,290 vs. Aberdeen, 20 February 2000 |
| Lowest Attendance: | 635 vs. Clydebank, 14 September 1999 |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
See main article: 1999–2000 Scottish First Division.
| Match Day | Date | Opponent | H/A | Score | ICT Scorer(s) | Attendance |
|---|---|---|---|---|---|---|
| 1 | 7 August | Dunfermline Athletic | A | 0–4 | 4,677 | |
| 2 | 14 August | Falkirk | H | 2–3 | Sheerin, Tokely | 3,022 |
| 3 | 21 August | St Mirren | A | 2–3 | Sheerin, Teasdale | 3,040 |
| 4 | 28 August | Ayr United | A | 0–1 | 2,157 | |
| 5 | 4 September | Greenock Morton | H | 1–1 | Glancy | 2,414 |
| 6 | 11 September | Clydebank | H | 1–0 | Sheerin | 1,697 |
| 7 | 18 September | Livingston | A | 2–2 | Bavidge, Sheerin | 2,584 |
| 8 | 25 September | Raith Rovers | H | 0–2 | 2,961 | |
| 9 | 2 October | Airdrieonians | A | 1–1 | Glancy | 2,097 |
| 10 | 16 October | Falkirk | A | 2–0 | Wyness, McLean | 2,403 |
| 11 | 23 October | Dunfermline Athletic | H | 1–1 | Bavidge | 3,006 |
| 12 | 30 October | Clydebank | A | 3–0 | Sheerin, Teasdale, Wilson | 220 |
| 13 | 6 November | Livingston | H | 2–0 | 2,474 | |
| 14 | 12 November | Greenock Morton | A | 1–5 | Tokely | 812 |
| 15 | 27 November | Airdrieonians | H | 2–0 | Wilson, Xausa | 2,022 |
| 16 | 30 November | Ayr United | H | 1–1 | Christie | 1,073 |
| 17 | 4 December | Raith Rovers | A | 2–4 | Sheerin, Bavidge | 1,971 |
| 18 | 11 December | St Mirren | H | 1–1 | Wilson | 2,893 |
| 19 | 18 December | Dunfermline Athletic | H | 0–1 | 3,775 | |
| 20 | 27 December | Clydebank | H | 4–1 | Sheerin (2), Wilson (2) | 1,640 |
| 21 | 3 January | Livingston | A | 1–1 | Wilson | 2,656 |
| 22 | 8 January | Greenock Morton | H | 6–2 | Wilson (2), Byers, Bavidge, Sheerin, Tokely | 1,524 |
| 23 | 22 January | Raith Rovers | H | 1–1 | Glancy | 2,302 |
| 24 | 5 February | Airdrieonians | A | 4–1 | 1,597 | |
| 25 | 12 February | St Mirren | A | 0–2 | 3,742 | |
| 26 | 26 February | Falkirk | H | 0–3 | 2,727 | |
| 27 | 4 March | Clydebank | A | 1–0 | Wyness | 168 |
| 28 | 7 March | Ayr United | A | 3–1 | Wilson, Sheerin, Xausa | 1,274 |
| 29 | 18 March | Livingston | H | 4–1 | Xausa (3), Wyness | 2,206 |
| 30 | 25 March | Ayr United | H | 1–1 | Wilson | 1,790 |
| 31 | 1 April | Greenock Morton | A | 2–0 | Wyness, Xausa | 567 |
| 32 | 8 April | Raith Rovers | A | 0–2 | 2,538 | |
| 33 | 15 April | Airdrieonians | H | 1–5 | Wyness | 1,404 |
| 34 | 22 April | Dunfermline Athletic | A | 1–2 | Xausa | 2,677 |
| 35 | 29 April | Falkirk | A | 2–2 | 4,449 | |
| 36 | 6 May | St Mirren | H | 5–0 | McCulloch (2), Xausa, Wilson, Bavidge | 3,218 |
See main article: 1999–2000 Scottish League Cup.
| Round | Date | Opponent | H/A | Score | ICT Scorer(s) | Attendance |
|---|---|---|---|---|---|---|
| R1 | 31 July | Stenhousemuir | A | 3–1 | 528 | |
| R2 | 17 August | St Mirren | H | 2–0 (aet) | 1,238 | |
| R3 | 12 October | Motherwell | H | 0–1 | 2,195 | |
See main article: 1999–2000 Scottish Challenge Cup.
| Round | Date | Opponent | H/A | Score | ICT Scorer(s) | Attendance |
|---|---|---|---|---|---|---|
| R1 | 10 August | St Mirren | H | 1–0 | 1,343 | |
| R2 | 24 August | Hamilton Academical | A | 3–0 | 298 | |
| QF | 14 September | Clydebank | H | 2–0 | 635 | |
| SF | 28 September | Livingston | H | 1–0 | Sheerin | 1,025 |
| Final | 21 November | Alloa Athletic | N | 4–4 (aet, Alloa won 5–4 on penalties) | Sheerin (3), Wilson | 4,047 |
See main article: 1999–2000 Scottish Cup.
| Round | Date | Opponent | H/A | Score | ICT Scorer(s) | Attendance |
|---|---|---|---|---|---|---|
| R3 | 8 February | Celtic | A | 3–1 | Wilson, Moravcik (own goal), Sheerin | 34,389 |
| R4 | 20 February | Aberdeen | H | 1–1 | Mann | 6,290 |
| R4 R | 29 February | Aberdeen | A | 0–1 | 18,451 | |
| Paul Sheerin | Scottish Challenge Cup Final | 4–4 | Alloa Athletic | 21 November 1999 | |
| Davide Xausa | Scottish First Division | 4–1 | Livingston | 18 March 2000 |