| Club: | Livingston |
| Season: | 1999–00 |
| Manager: | Ray Stewart (until 15 March) Jim Leishman |
| Stadium: | Almondvale Stadium |
| League: | Scottish First Division |
| League Result: | Fourth place |
| Cup1 Result: | Fourth round |
| Cup2 Result: | Second round |
| Cup3 Result: | Semi-final |
| League Topscorer: | David Bingham & Brian McPhee (15) |
| Season Topscorer: | David Bingham (19) |
| Pattern La1: | _blackborder_trim |
| Pattern B1: | _thinblacksides |
| Pattern Ra1: | _blackborder_trim |
| Pattern So1: | _2 black stripes |
| Leftarm1: | FFCC00 |
| Body1: | FFCC00 |
| Rightarm1: | FFCC00 |
| Shorts1: | 000000 |
| Socks1: | FFCC00 |
| Pattern La2: | _redborder |
| Pattern B2: | _thinredsides |
| Pattern Ra2: | _redborder |
| Pattern So2: | _2 red stripes |
| Shorts2: | FF0000 |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
Season 1999-00 saw Livingston compete in the Scottish First Division. They also competed in the Challenge Cup, League Cup and the Scottish Cup.
Season 1999–00 was Livingston's first season in the Scottish First Division having been promoted the previous season they finished fourth in the league.[1] They reached the semi-final of the challenge cup, were knocked out of the League Cup in the second round and the Scottish Cup in the fourth round.
Livingston started the season under Ray Stewart and on 15 March 2000 he was sacked by the club with Jim Leishman being re-appointed as manager.[2]
See main article: 1999–2000 Scottish First Division.
See main article: 1999–2000 Scottish League Cup.
See main article: 1999–2000 Scottish Challenge Cup.
See main article: 1999–2000 Scottish Cup.