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The 1998–99 Southern Football League season saw Nuneaton Borough win the Premier Division to earn 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 were relegated to the eighth level whilst Andover resigned and Brackley Town were expelled.
Cup competition
The league's cup competition, the Dr Martens League Cup, was won by Cambridge City who beat Sutton Coldfield Town 2–1 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 4–3 on aggregate to reach the final and Sutton Coldfield defeated Boston United 2–1 on aggregate to reach the final.