As a 21-year old Cambridge University undergraduate from Enfield, Middlesex, he made his debut on 31 October 1986 against David Whiting, prevailing with his solution to the crucial conundrum YUNIGNITE. Freeman won that game and seven more to achieve octochampdom with a then-record aggregate score of 523 points; a record that would stand for almost 14 years before it was beaten by David Williams in Series 43. In his second game, Freeman scored 82 points - not only the highest score of the series, but also then an all-time record. Freeman returned for the final rounds as the clear #1 seed, and dominated his opponents Elisabeth Jardine and Les Martin in the quarter-finals and semi-finals respectively, before going on to face Mike Percik in the grand final. Despite having outtakes ☓; disallowed in the second round, Freeman would enter a commanding performance here too, running out the 96 – 52 winner.
In February 1987, Freeman appeared on the special episode to celebrate Countdown's 500th show. Later the same year, he returned for Championship of Champions III, and after beating Michael Stephenson and John Clarke, he found a tough opponent in the grand final in the shape of David Trace. Freeman lost out in the first conundrum to Trace, putting him ten points behind, but he scored in every other round, including the final, crucial conundrum, to win 115 – 107 — the highest ever score in a 14-round grand final and the only time anyone has ever scored over 110 under that format. Freeman became the first ever grand slam winner by winning all his games.
In 1996, Freeman returned to the Countdown studios one last time to participate in the Supreme Championship. Given a bye in the first round, Freeman defeated Ian Bebbington in the second round and Barry Grossman in a closely-fought group final to put himself into the series quarter-finals. There, he beat Andrew Perry before once again beating John Clarke in the semi-final. In the final, he faced Allan Saldanha in what promised to be a true battle of the greats. However, as it turned out, Freeman managed to spot a 9 letter word in the first round that Saldanha didn't, and was able to hold on to his lead to win 82 – 79, winning the title of 'all-time supreme champion', and maintaining his winning streak at an unprecedented 19 games (his only ever loss being against producer Mark Nyman in the separate Countdown Masters series in 1990). Notably, all but one of Freeman's Supreme Championship games were decided by crucial conundrums.
- Second highest total wins on Countdown (19). He was top of the pile for many years, until finally overtaken by Conor Travers in the final of the 30th Birthday Championship.
- Highest score for a 14-round game (115).
- Second highest score for a 9-round game (82). It was the highest score at the time he made it. It's also the highest score by a champion, neither the score by Allan Saldanha nor by Stephen Balment were made whilst they were the sitting champion.
- Second highest 8-game total (523). It was the highest score at the time he made it.
- Highest debut score of Series 10.
- Series 10 winner.
- Championship of Champions III winner.
- Series 33 (Supreme Championship) winner.
Freeman has also been a top Scrabble player.
|Champion of Champions
Championship of Champions III
|#||Date||Type||Contestant 1||Score||Contestant 2||Guest||Lex||Max|
|459||31/10/1986||P||Harvey Freeman||65 – 45||David Whiting||Lee Peck||Freda Thornton||86|
|460||3/11/1986||P||Harvey Freeman||82 – 30||Rita Meston||Lee Peck||Freda Thornton||83|
|461||4/11/1986||P||Harvey Freeman||60 – 29||Anilkumar Shah||Lee Peck||Freda Thornton||72|
|462||5/11/1986||P||Harvey Freeman||57 – 33||Michael Sim||Lee Peck||Freda Thornton||71|
|463||6/11/1986||P||Harvey Freeman||64 – 28||John Wesley||Lee Peck||Freda Thornton||73|
|464||7/11/1986||P||Harvey Freeman||49 – 21||Frances Kitsall||Lee Peck||Freda Thornton||73|
|465||10/11/1986||P||Harvey Freeman||71 – 17||Martin Reed||Bill Tidy||Freda Thornton||83|
|466||11/11/1986||P||Harvey Freeman||75 – 10||Roy James||Bill Tidy||Freda Thornton||76|
|488||11/12/1986||QF||Harvey Freeman||65 – 29||Elisabeth Jardine||Bill Tidy||Catherine Clarke||73|
|492||17/12/1986||SF||Harvey Freeman||76 – 36||Les Martin||Bill Tidy||Catherine Clarke||??|
|494||19/12/1986||GF||Harvey Freeman||96 – 52||Mike Percik||Gyles Brandreth, Bill Tidy||Della Thompson||117|
|595||22/06/1987||CQF||Harvey Freeman||44 – 36||Michael Stephenson||Sally James||Della Thompson||??|
|599||26/06/1987||CSF||Harvey Freeman||45 – 38||John Clarke||Sally James||Della Thompson||71|
|601||30/06/1987||CGF||Harvey Freeman||115 – 107||David Trace||Sally James||Della Thompson||127|
|M45||5/2/90-9/2/90||Masters 1||Mark Nyman||76 – 68||Harvey Freeman||N/A||Catherine Clarke||132|
|1872||1/11/1996||cSF||Ian Bebbington||54 – 72||Harvey Freeman||Geoffrey Durham||Susie Dent||85|
|1874||5/11/1996||cF||Barry Grossman||37 – 44||Harvey Freeman||Geoffrey Durham||Susie Dent||73|
|1902||13/12/1996||SQF||Andrew Perry||44 – 54||Harvey Freeman||Jenny Hanley||Susie Dent||72|
|1905||18/12/1996||SSF||John Clarke||48 – 65||Harvey Freeman||Nigel Rees||Catherine Clarke||72|
|1907||20/12/1996||SGF||Allan Saldanha||79 – 82||Harvey Freeman||Nigel Rees||Catherine Clarke||127|
|Championship of Champions Winners|
I : Mark Nyman | II : Clive Freedman | III : Harvey Freeman | IV : Nic Brown | V : Tim Morrissey | VI : Wayne Summers | VII : Don Reid | VIII : Chris Rogers | IX : Natascha Kearsey | X : Scott Mearns | XI : Graham Nash | XII : Paul Gallen | XIII : Steve Briers | XIV : Dylan Taylor | XV : Zarte Siempre