Three men’s seeds crashed out on Friday in the Brisbane International quarter-finals.

Bulgarian world No.48 Grigor Dimitrov ousted seventh-seeded Austrian Jurgen Melzer 6-3 6-2 in just under an hour.

And fourth seed, Ukraine’s Alexandr Dolgopolov, lost to fifth seed Kei Nishikori of Japan 6-4 7-6 (7-3).

Earlier on Friday, former Australian Open finalist Marcos Baghdatis became the first man into the semi-finals by upsetting third-seeded Frenchman Gilles Simon 6-3 6-4.

At 21, Dimitrov was the youngest player left in the Brisbane men’s draw – and at 31, world No.29-ranked Melzer was the oldest.

Dimitrov – the youngest player in the world top 50 at year’s end – showed the form that had already accounted for second-seeded Canadian Milos Raonic in Brisbane.

Dimitrov will line up against Baghdatis in the semi-finals on Saturday.

World No.36 Baghdatis – ranked 20 places lower than Simon – maintained his Midas touch in Australia with the victory on Pat Rafter Arena.

Baghdatis, 27, extended his record Down Under to 38-14, which includes his sole grand slam final appearance in 2006 and his last ATP World Tour title in Sydney three years ago.

The Cypriot has not dropped a set on his way to booking his maiden Brisbane International semi-final appearance.

Meanwhile, world No.18 Dolgopolov had made last year’s Brisbane International final but had no answer to 19th-ranked Nishikori on Friday.

Nishikori, 23, will take on the winner of top seed and defending champion Andy Murray’s quarter-final against Uzbekistan’s Denis Istomin.