| Club: | Hibernian |
| Season: | 1999–2000 |
| Manager: | Alex McLeish |
| League: | SPL |
| League Result: | 6th |
| Cup1: | Scottish Cup |
| Cup1 Result: | Semi |
| Cup2: | League Cup |
| Cup2 Result: | R3 |
| League Topscorer: | Miller, 11 |
| Season Topscorer: | Miller, 13 |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
| Highest Attendance: | 16976 |
| Lowest Attendance: | 9211 |
| Average Attendance: | 12070[1] (up 1637) |
Season 1999–2000 was Hibs' first season back in the top flight of Scottish football, the newly founded Scottish Premier League, after gaining promotion from the First Division in 1999. Hibs re-established themselves well in the top flight, finishing in sixth place. The club also had a good Scottish Cup run, but were disappointingly beaten 2–1 by Aberdeen, who finished bottom of the SPL, in the semi-final at Hampden Park. The season was also memorable for Hibs fans due to a 3–0 win in the "Millennium derby" against Hearts. There was a landmark day towards the end of the season, as the last game on the Easter Road slope was played.[2]
As a club newly promoted to the SPL, Hibs entered at the second round stage of the competition, in which they defeated Clyde in a penalty shootout. This win sent Hibs through to a third round match against Kilmarnock at Rugby Park. In that match, Hibs conceded two early goals, and despite efforts by Pat McGinlay and Kenny Miller, Kilmarnock ran out 3–2 winners.
| Player | From | Fee |
|---|---|---|
 Dirk Lehmann | Fulham | Free |
| Tom Phillips | Derby County | Free |
| Colin Morton | Derby County | Free |
| Ian Murray | Dundee United | Free |
 Fabrice Henry | FC Basel | Free |
| Mathias Jack | Fortuna Düsseldorf | Free |
 Nick Colgan | Bournemouth | Free |
| Grant Brebner | Reading | Free |
| Martin McIntosh | Stockport County | £250,000 |
| Player | To | Fee |
|---|---|---|
| Chris Jackson | Cowdenbeath | Free |
| David Elliot | Partick Thistle | Free |
| Brian Welsh | Stenhousemuir | Free |
 Peter Guggi | Retired | Free |
| Eric Paton | Partick Thistle | Free |
| Paul Riley | Brechin City | Free |
| Paul Tosh | Raith Rovers | Free |
| Jason Gardiner | Stirling Albion | Free |
| Justin Skinner | Dunfermline Athletic | Free |
| Barry Lavety | St Mirren | Nominal fee |
| Stephen Crawford | Dunfermline Athletic | Free |
 Olafur Gottskalksson | Brentford | Free |
| Alex Marinkov | Retired | Free |
| Fabrice Henry | Retired | Free |
| Paul Holsgrove | Darlington | Free |
 Earl Jean | W Connection | Free |
During the 1999–2000 season, Hibs used 29 different players in competitive games. The table below shows the number of appearances and goals scored by each player.[3]
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