| Competition: | Macedonian First League |
| Season: | 1998–99 |
| Winners: | Sloga Jugomagnat 1st domestic title |
| Relegated: | Skopje Balkan |
| Continentalcup1: | Champions League |
| Continentalcup1 Qualifiers: | Sloga Jugomagnat |
| Continentalcup2: | UEFA Cup |
| Continentalcup2 Qualifiers: | Sileks Vardar |
| Continentalcup3: | Intertoto Cup |
| Continentalcup3 Qualifiers: | Pobeda Cementarnica |
| League Topscorer: | Rogério Oliveira (22 goals) |
| Dates: | 9 August 1998 – 29 May 1999 |
| Biggest Home Win: | Sileks 7–1 Balkan Pobeda 6–0 Skopje Sileks 6–0 Skopje Vardar 6–0 Tikvesh Borec 6–0 Balkan |
| Biggest Away Win: | Pelister 0–5 Sloga |
| Highest Scoring: | Vardar 7–2 Balkan |
| Matches: | 182 |
| Total Goals: | 534 |
| Prevseason: | 1997–98 |
| Nextseason: | 1999–2000 |
The 1998–99 Macedonian First League was the 7th season of the Macedonian First Football League, the highest football league of Macedonia. The first matches of the season were played on 9 August 1998 and the last on 29 May 1999. Sileks were the defending champions, having won their third title in a row. The 1998-99 champions were Sloga Jugomagnat who had won their first title.
Relegated to 1998–99 Second League
|
Relegated to 1999–2000 Second League
|
| Rank | Player | Club | Goals |
|---|---|---|---|
| 1 |  Rogério Oliveira | Pobeda | 22 |
| 2 | Vancho Trajchev | Vardar | 14 |
Source: Top15goalscorers.blogspot.com