"Monkey's" time at Swindon was interrupted by injury and he was loaned to Hartlepool United. Following a successful loan spell, a deal was then agreed between Swindon and Hartlepool on January 10 for Monkhouse to sign for the latter for an undisclosed fee. Ironically, when Monkhouse played for Hartlepool against Swindon on 3 February 2007 he scored the winning goal against his former side. Remarkably, the first time he was on the losing side in a league match in 2006/7 was in Hartlepool's defeat against Barnet on 7 April 2007 - his 32nd appearance of the season.
Monkhouse was named in the PFA League Two Team of the Year for the 2006-07 season. Having earned the initial nickname 'Monkey', for obvious reasons, this has evolved into various forms over the years, such as 'Monks' and 'Monkmanaman' - taken from has likening, in looks and style of play, to Steve Mcmanaman.