Mark Allen missed out on a place in the last 16 of the Gibraltar Open after being beaten 4-3 by Robert Milkins.

The Antrim man had been 3-1 ahead but his failure to take his chances in the fifth came back to haunt him as Milkins hit breaks of 94 and 76 to take the last three frames.

Earlier, Allen had beaten Mark Joyce and Steven Hallworth to progress.

Meanwhile, Fergal O'Brien and Leo Fernandez both lost final-frame deciders as they exited the tournmant.

O'Brien, who is currently fighting for tour survival in 60th position on the one-year ranking list, led Mitchell Mann 1-0 and 2-1, before battling back to 3-3. But Mann then found his form, knocking in a 104 break to progress.

Fernandez pushed world number 26 Joe Perry all the way before his 4-3 defeat.

Gerard Greene was beaten 4-1 by former world champion Stuart Bingham, who finished off the match in style with a maximum 147 break, just the second in the history of the tournament.

Ronnie O'Sullivan crashed out in the opening round, suffering a 4-3 loss to Ben Woollaston.

It leaves Jordan Brown, who progressed to the last 16 yesterday, as the sole Irish player left in the tournament after defeats for Aaron Hill (last 32) and Ken Doherty (last 64).