The 1998–99 season was the 28th in the history of Essex Senior Football League a football competition in England.[1]
The league featured 14 clubs which competed in the league last season, no new clubs joined the league this season.
Bowers United were champions, winning their second Essex Senior League title, while Great Wakering Rovers were promoted to the Isthmian League.
| Competition: | Essex Senior Football League |
| Season: | 1998–99 |
| Winners: | Bowers United |
| Promoted: | Great Wakering Rovers |
| Matches: | 182 |
| Total Goals: | 642 |
| League Topscorer: | David Hope (45 goals) |
| Prevseason: | 1997–98 |
| Nextseason: | 1999–2000 |