He was from Bickerstaff, Lancashire, and first appeared on 18 February 1995 beating Tony David 69 – 38 on his début, which also happened to be the second ever max game in the show's history. Shacklady went on to win four more games before losing to Tim Dickinson 63 – 52, but his scores — he averaged almost 65 points a game, which if he had completed his octochamp run, would have put him on a par with Harvey Freeman — saw him return for the finals as #3 seed. Shacklady beat Barry Hughes and Andy Cusworth on his way to the final against Chris Rogers. Shacklady dominated the final, winning 105 – 63 to become the 29th champion of Countdown.
Shacklady was a favourite for Championship of Champions VIII in 1996, where he beat Satbir Gupta in the first round before losing narrowly to Kenneth Michie in the semi-finals after neither player solved the crucial conundrum.
|#||Date||Type||Contestant 1||Score||Contestant 2||Guest||Lex||Max|
|1621||16/02/1995||P||Darren Shacklady||69 – 38||Tony David||Jan Harvey||Ruth Killick||69|
|1622||17/02/1995||P||Darren Shacklady||72 – 23||Liz Rickets||Jan Harvey||Ruth Killick||75|
|1623||20/02/1995||P||Darren Shacklady||68 – 41||Peter Andrews||Nigel Rees||Ruth Killick||74|
|1624||21/02/1995||P||Darren Shacklady||55 – 26||Brenda Thomson||Nigel Rees||Ruth Killick||75|
|1625||22/02/1995||P||Darren Shacklady||73 – 41||Conor Martin||Nigel Rees||Ruth Killick||75|
|1626||23/02/1995||P||Darren Shacklady||52 – 63||Tim Dickinson||Nigel Rees||Ruth Killick||73|
|1648||27/03/1995||QF||Darren Shacklady||66 – 43||Barry Hughes||Pete Murray||Richard Samson||71|
|1651||30/03/1995||SF||Andy Cusworth||46 – 51||Darren Shacklady||David Jacobs||Richard Samson||68|
|1652||31/03/1995||GF||Chris Rogers||63 – 105||Darren Shacklady||David Jacobs, Pete Murray||Richard Samson||117|
|1851||3/10/1996||CQF||Darren Shacklady||45 – 34||Satbir Gupta||Jan Harvey||Susie Dent||69|
|1853||7/10/1996||CSF||Kenneth Michie||46 – 40||Darren Shacklady||Jan Harvey||Susie Dent||66|