| Club: | Hibernian |
| Season: | 1998–99 |
| Manager: | Alex McLeish |
| League: | SFL First Division |
| League Result: | 1st (promoted) |
| Cup1: | Scottish Cup |
| Cup1 Result: | R3 |
| Cup2: | League Cup |
| Cup2 Result: | Quarter |
| League Topscorer: | Crawford, 14 |
| Season Topscorer: | Crawford, 15 |
| Prevseason: | 1997–98 |
| Nextseason: | 1999–00 |
| Highest Attendance: | 14801 |
| Lowest Attendance: | 8649 |
| Average Attendance: | 10433[1] (down 1592) |
Season 1998–99 was a successful season for Hibernian F.C. as the club got promoted on their first attempt and achieved a record number of points, following their relegation from the Scottish Premier League the year prior.[2] There was disappointment in the cup competitions, however, as the club were beaten by Stirling Albion in the Scottish Cup, and were defeated convincingly 4–0 by St Johnstone in the League Cup. As a First Division club, Hibs would have entered the Scottish Challenge Cup, but the competition was not played during the 1998–99 season due to a lack of sponsorship.[3]
| Player | From | Fee |
|---|---|---|
| Bryan Gunn | Norwich City | Free |
 Stuart Lovell | Reading | Free |
| Paul Holsgrove | Brighton & Hove Albion | £110,000 |
 Mixu Paatelainen | Wolverhampton Wanderers | £75,000 |
| Paul Lovering | Clydebank | £100,000 |
| Derek Collins | Greenock Morton | £120,000 |
| Paul Hartley | Raith Rovers | £250,000 |
| Tom Smith | Clydebank | Free |
 Franck Sauzee | Montpellier HSC | Free |
| Alex Marinkov | Scarborough | £25,000 |
| Player | To | Fee |
|---|---|---|
| Jamie McQuilken | Falkirk | Free |
| Andy Dow | Aberdeen | £80,000 |
| Darren Dods | St Johnstone | £70,000 |
| Willie Miller | Dundee | Free |
| Graeme Donald | Stirling Albion | Free |
| Gordon Hunter | Canberra Cosmos | Free |
| Stuart McCaffrey | Aberdeen | Free |
 Jimmy Boco | Retired | Free |
| Ian McDonald | Stenhousemuir | Free |
| John Martin | East Fife | Free |
| Kevin Harper | Derby County | £300,000 |
 Bjarni Larusson | Walsall | Free |
| Tony Rougier | Port Vale | £175,000 |
| Rab Shannon | East Fife | Free |
 Klaus Dietrich | Free | |
| Bryan Gunn | Retired | Free |
| Player | To |
|---|---|
| Paul Riley | Brechin City |
| Paul Tosh | Partick Thistle |
| Kenny Miller | Stenhousemuir |
 Emilio Bottiglieri | Albion Rovers |
| David Elliot | Wigan Athletic |
| Paul Tosh | Exeter City |
| Russell Huggon | Stenhousemuir |
| Jamie Carter | East Stirlingshire |
During the 1998–99 season, Hibs used 34 different players in competitive games. The table below shows the number of appearances and goals scored by each player.[4] Goalkeeper Olafur Gottskalksson played in every competitive match.
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