Sandwiched in between those wins came a third career defeat for Pickering, travelling to the Canary Islands to challenge Spaniard Alejandro Monzon and dropping a split decision.
One more defence of his Commonwealth title took place on 24 October 2003 with Pickering retaining the belt by beating Ghana's Alfred Tetteh at the York Hall.
[14] Pickering would defend the belt twice more against Juan Garcia Martin[15] in May 2004 and Miguel Mallon in June 2005, the latter victory taking place in Madrid.
In an exciting contest Pickering eventually went home empty handed dropping a majority decision for his fourth career defeat in a fight which took place in Hunter's backyard, the Borough Hall in Hartlepool.
[16] on 16 March 2007 Pickering once again challenged for the now vacant British title and lifted the belt for the second time, defeating Marc Callaghan at the Norwich Showground.
[19] His next fight saw a move up to featherweight and another chance at a British title against another prospect in Scotland's Paul Appleby only to drop another 12-round decision in Glasgow for the 8th defeat of his career.
[20] Pickering returned to the ring on 23 May 2009 to defeat journeyman Sid Razak in Sleaford, Lincolnshire and followed this by traveling to Ukraine for an unexpected chance to regain the European title.