Having overcome a career-threatening injury to his left knee in November 1999, Hipkiss made his first start for the Tigers' U21s against Leeds on 9 November 2001, scoring a try on his debut. He was called into the first team squad for summer training in 2002 and had his Premiership debut away at Leeds that year. Hipkiss was one of five Leicester players called up for the 2003 IRB U21 World Cup. He was chosen for the England Sevens squad in 2004. He quickly became a regular member of the successful Tigers 2002–03 U21 team, and captained a Leicester side in the 2006 Middlesex Sevens at Twickenham.
Breakout season and World Cup
Initially Hipkiss struggled to break into Leicester's starting team before playing twelve times in the 2005-06 season. The following year was to be his breakout year playing thirty games for Leicester and being named Tigers Players' Player of the Year in 2006-07. That year he won his first Premiership medal, starting the final as Leicester defeated Gloucester. Hipkiss made his debut on 4 August 2007 in a 62-5 win against at Twickenham in a warm up test for the 2007 Rugby World Cup. He was named in England's 2007 Rugby World Cup squad and played in group stages matches against and. He was not involved in the quarter final but replaced an injured Josh Lewsey before half time in the semi final win over. Hipkiss was a substitute for the 2007 Rugby World Cup Final against and replaced Jason Robinson in the second half as England lost 15-6.
Injuries and 2010 title win
Returning from the World Cup Hipkiss played regularly for Leicester but missed January with a groin injury and subsequently was left out of the England Squad for the 2008 Six Nations Championship. Hipkiss started both the 2008 Premiership Final against Wasps and the 2008 Anglo-Welsh Cup Final against Ospreys which Leicester lost. On 20 May 2008 he was selected for England's squad to play against, however he was injured in the Premiership final with a fractured cheekbone. This injury meant Hipkiss missed the tour to New Zealand. 2008-09 saw the Tigers feature in two finals with Hipkiss again starting both. He played 12 as Leicester beat London Irish 10-9 in the 2009 Premiership Final and again the next week as Leicester lost the 2009 Heineken Cup Final to Leinster 19-16. Hipkiss' form in these matches saw him start both summer Tests for against. He played in the 2009 Autumn International against, in the centre with former Tigers clubmate Ayoola Erinle his partner in both 2009 finals for Leicester. During the 2009–10 season, Hipkiss suffered an injury midway through the season, but returned to play for Tigers' A-league side in their semi-final against the Saracens' A-league side. He scored a try, and the team won 23–11. He went on to score a further try in the final, where the team won the 'A' league. He continued his streak of tries when playing as a substitute in the 2010 Premiership Final, again against Saracens. Tigers went one point behind four minutes from time, and Hipkiss wriggled through an attempted tackle from the retiring Glen Jackson to score the winning try, to leave the game at 33–27.
Bath
Hipkiss joined Bath on a 2-year contract from the 2011-2012 season. After a two-year spell with Bath a shoulder injury forced Hipkiss to retire in May 2013.
Post career life
After retiring from rugby Hipkiss worked in a professional kitchen as a chef before training to become a project manager in the building trade.
