A customs and excise officer from Halesowen in the West Midlands, he first appeared on 1 November 1985, soundly defeating Michael Spencer 66 – 16. After two more wins, his reign as champion was cut short by Marion Johnstone, but his impressive scores had been enough to earn him a place in the final rounds as #5 seed. He defeated Robert Coton in the quarter-finals after another impressive performance, before pulling off a major upset in beating #1 seed Clive Freedman in the semis by just three points. In the grand final against Julian Hough, Bebbington led 82 – 77 going into the conundrum. Neither contestant was able to unscramble TEEUPLATE in the time, meaning Bebbington became the seventh series champion.
Bebbington returned to Countdown in 1996 for the Supreme Championship, defeating James Sinclair in the first round but losing to the ultimate winner Harvey Freeman in his next and final match. The score had been 62 – 54 in Freeman's favour making it a crucial conundrum, and Bebbington actually buzzed first. However, no upset took place as he gave the incorrect solution of CONCEITED. Freeman went on to correctly get CONTENTED and win by 18 points.
In 1988, he appeared on the first series of Fifteen to One.
|#||Date||Type||Contestant 1||Score||Contestant 2||Guest||Lex||Max|
|303||1/11/1985||P||Michael Spencer||16 – 66||Ian Bebbington||Steve Jones||??|
|304||4/11/1985||P||Ken Brown||31 – 52||Ian Bebbington||Steve Jones||??|
|305||5/11/1985||P||Michael McCormack||18 – 59||Ian Bebbington||Steve Jones||??|
|306||6/11/1985||P||Marion Johnstone||52 – 41||Ian Bebbington||Steve Jones||??|
|335||17/12/1985||QF||Robert Coton||53 – 65||Ian Bebbington||Richard Stilgoe||Della Thompson||73|
|336||18/12/1985||SF||Clive Freedman||46 – 49||Ian Bebbington||Richard Stilgoe||Della Thompson||70|
|338||20/12/1985||GF||Ian Bebbington||82 – 77||Julian Hough||Richard Stilgoe,|
|401||3/04/1986||CQF||John Wallace||59 – 38||Ian Bebbington||Gyles Brandreth||Catherine Clarke||82|
|M101||4/03/1991-8/03/1991||M||Ian Bebbington||99 – 86||Andrew Guy||none||Freda Thornton||???|
|1869||29/10/1996||cQF||Ian Bebbington||45 – 36||James Sinclair||June Whitfield||Susie Dent||73|
|1872||1/11/1996||cSF||Ian Bebbington||54 – 72||Harvey Freeman||Geoffrey Durham||Susie Dent||85|