Webb notched up a run of 5 wins in the heats before losing his 6th game to eventual runner-up Robert Teuton. Webb qualified for the finals as No. 4 seed, dispatching No. 5-ranked Una Szewc before losing to octochamp and eventual series champion Chris Waddington.
Webb is also a Scrabble Grandmaster, and finished runner-up in the National Scrabble Championship on 18 October 2009, beaten by Countdown's Series 57 champion Craig Beevers. He is known as "Dweebovision" on YouTube  and regularly uploads videos of himself playing the game on Internet Scrabble Club and in face-to-face tournaments in the UK and around the world. In 2019, he and fellow Scrabbler Bob Violett set a new record for the highest combined score in a tournament game: 1,213 points. 
Webb is also a crossword buff, having contested The Times Crossword Championship in 2019. He has appeared on numerous game shows; he won a house on ITV's Raise the Roof, and won an impressive 30 times on 100%.
|#||Date||Type||Contestant 1||Score||Contestant 2||Presenters||Guest||Lex||Max|
|1149||23/07/1991||P||David Webb||53 – 23||Anne Lyng||Richard Whiteley||Carol Vorderman||Sheridan Morley||Richard Samson||83|
|1150||24/07/1991||P||David Webb||50 – 21||Hattie Ison||Richard Whiteley||Carol Vorderman||Sheridan Morley||Richard Samson||73|
|1151||25/07/1991||P||David Webb||61 – 39||Jackie Watson||Richard Whiteley||Carol Vorderman||Sheridan Morley||Richard Samson||74|
|1152||26/07/1991||P||David Webb||52 – 18||Harry Victor||Richard Whiteley||Carol Vorderman||Sheridan Morley||Richard Samson||73|
|1153||29/07/1991||P||David Webb||43 – 40||Andrew Mitchell||Richard Whiteley||Carol Vorderman||Sheridan Morley||Richard Samson||80|
|1154||30/07/1991||P||David Webb||41 – 64||Robert Teuton||Richard Whiteley||Carol Vorderman||Frazer Hines||Alexandra Clayton||72|
|1194||24/09/1991||QF||Una Szewc||47 – 65||David Webb||Richard Whiteley||Carol Vorderman||Martin Jarvis||Richard Samson||75|
|1195||25/09/1991||SF||Chris Waddington||60 – 56||David Webb||Richard Whiteley||Carol Vorderman||Martin Jarvis||Richard Samson||83|
|5620||14/01/2013||30BP||Darryl Francis||86 – 68||David Webb||Nick Hewer||Rachel Riley||Martin Lewis||Susie Dent||119|