He co-created the format for the show, which has remained unchanged for over 20 years, with Senior Producer Rik Dovey, a lieutenant of then Sky Sports chief David Hill.
From the mid-1990s Sky boosted their boxing coverage by signing up most of the biggest names in Britain and the United States and Dempsey fronted all of the major shows either on regular subscription or Pay Per View Channels.
[3] For a period Sky enjoyed a near monopoly on the sport’s biggest names including Lennox Lewis, Evander Holyfield, Mike Tyson, Nigel Benn, Chris Eubank, Steve Collins and Naseem Hamed.
In 2007, he was nominated for an Irish Film and Television Academy Award for his hosting of the Rugby World Cup, an event which significantly enhanced the channel's reputation.
[7] The 2010 FIFA World Cup gave him the chance to continue his long association, on Australian TV with SBS,[8] the main broadcaster of the sport in the pacific region.
[9] In 2012, Dempsey presented every game at Euro 2012 on Setanta, alongside pundits Dietmar Hamann, Gary McAllister, Dennis Wise, David O'Leary and Andy Cole.
For the London Olympics Dempsey was invited to join the IOC's broadcasting arm, OBS, in their 10-channel, 3-language, 18-hour-per-day Live service, assisting former chief BBC sports producer John Shrewsbury in an editorial and production supervisor's role.
For pay network Primetime he hosted the ill-fated ring return of Ricky Hatton in Manchester[10] and, for ESPN, Wladimir Klitschko's world title defence, alongside co-host David Haye.
At the start of 2015-16 he presented BT Sport's opening game, the Community Shield, Arsenal v Chelsea from Wembley with Glenn Hoddle, Rio Ferdinand and Ian Wright and on the opening weekend of the premier league campaign was commentator at Old Trafford for Manchester United v Tottenham Hotspur in the first ever Ultra High Definition broadcast of its kind.
[14] As presenter of Boxing Tonight he fronted all BT Sport's boxing output, additionally acting as presenter for the return of David Haye at the O2 Arena which drew a record 3 million audience to UK TV and, for Channel 5, was anchor for the controversial Wembley Middleweight Title fight between Chris Eubank, jnr and Nick Blackwell.
At the end of the season he was hired by FIFA affiliate HBS to provide commentary on the Confederations Cup in Russia, including the opening ceremony in St Petersburg.
In addition to his broadcasting commitments at the Brazil World Cup in 2014 he co-headed the operations of Union Filmes, the Brazil-based production company in which he is a partner.