[2] During his early years with Hampshire, Middleton found his opportunities limited by Hampshire possessing arguably the strongest batting line-up in their history, consisting of international batsmen David Gower, Gordon Greenidge, Trevor Jesty, Paul Terry, and the Smith brothers Robin and Chris.
[1] The 1989 season saw make his debut in List A one-day cricket against Worcestershire at Bournemouth in the Refuge Assurance League,[3] alongside six appearances in the County Championship.
[4] Middleton played in two winning one-day finals in the 1991 NatWest Trophy and the 1992 Benson & Hedges Cup,[3] joint top-scoring (78) with Robin Smith in the former.
[6] His form in 1992 led to him being named The Cricket Society's Player of the Year and selection for that winter's England A tour to Australia.
[4] In his final season in 1995, he featured in just two first-class matches, against Warwickshire in the County Championship, and the touring West Indians.
[11] Alongside these roles, he played at club level for the Hampshire Academy, captaining them to promotion to the top division of the Southern Premier League.