The 1998âÂÂ99 Southern Football League season was the 96th in the history of the league, an English football competition.
Nuneaton Borough won the Premier Division and earned promotion to the Football Conference. Hastings Town, Gresley Rovers and Bromsgrove Rovers were relegated from the Premier Division, whilst Havant & Waterlooville, Clevedon Town, Margate and Newport County were promoted from the Southern and Midland Divisions, the former two as champions. Bloxwich Town and Brackley Town were relegated to the eighth level whilst Andover resigned from the league.
At the end of the season Midland Division was renamed Western Division, and Southern Division was renamed Eastern Division.
The Premier Division consisted of 22 clubs, including 18 clubs from the previous season and four new clubs:
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The Midland Division consisted of 22 clubs, including 16 clubs from the previous season and six new clubs:
At the end of the season Midland Division was renamed Western Division.
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The Southern Division consisted of 22 clubs, including 13 clubs from the previous season and nine new clubs, relegated from the Premier Division:
At the end of the season Southern Division was renamed Eastern Division.
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The league's cup competition, the Dr Martens League Cup, was won by Cambridge City who beat Sutton Coldfield Town 2âÂÂ1 on aggregate in the final. The first round, semi-finals and final were played over two legs with the second, third and fourth rounds going to a replay if the tie finished all square. Cambridge had beaten Dorchester Town 4âÂÂ3 on aggregate to reach the final and Sutton Coldfield defeated Boston United 2âÂÂ1 on aggregate to reach the final.