The 1999 Supertaça Cândido de Oliveira was the 21st edition of the Supertaça Cândido de Oliveira, the annual Portuguese football season-opening match contested by the winners of the previous season's top league and cup competitions (or cup runner-up in case the league- and cup-winning club is the same). The 1999 Supertaça Cândido de Oliveira was contested over two legs, and opposed Porto of the Primeira Liga and Beira-Mar of the Liga de Honra. Porto qualified for the SuperCup by winning the 1998–99 Primeira Divisão, whilst Beira-Mar qualified for their first Supertaça by winning the 1998–99 Taça de Portugal.[7][8]
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The first leg was televised on RTP, whilst the second leg was televised on TVI.[9][10] The first leg which took place at the Estádio Mário Duarte, saw Porto defeat the Auri-negros 2–1 thanks to late strike from Esquerdinha.[11][12][13] The second leg which took place at the Estádio das Antas, saw the Dragões defeat the Aveiro side and thus claim an eleventh Supertaça.[14][15][16]