[7] Cherry started his career with a five-day trial at Derby County, having been scouted by Ernie Roberts playing for Calverton Youth Wing in a 7–1 defeat to Ilkeston U16s.
[8] He was on the bench for the first round of the UEFA Cup against Irish club Finn Harps in the 1976–77 season due to Colin Boulton being out on loan and Steve Bowtell being illegible.
[8] Cherry started his first competitive game for Derby as John Middleton was ruled unfit due to a shoulder injury for a First Division fixture against Southampton at the Baseball Ground on 16 February 1980.
[2] Manager John McGrath had sold regular custodian Trevor Dance, and was forced to enter the loan market after Mark Harrison was struck down with injury.
[8] New manager Peter Taylor kept Cherry in goal, who would save a penalty from Kevin Keegan in a 1–0 defeat to Newcastle United at St James' Park on 27 December.
[8] Derby performed well in the FA Cup, though, and Cherry kept a clean sheet in a 0–0 draw away at Plymouth Argyle in the sixth round, denying Gordon Staniforth on multiple occasions.
[18] However, he conceded directly from a corner kick in the replay and felt "lower than the village idiot", whilst goalscorer Andy Rogers admitted the goal was "an absolute fluke".
[22] Walsall beat Preston North End 7–3 and Port Vale 2–1 (after a replay) to reach the third round of the FA Cup against First Division club Manchester City on 4 January 1986.
[22] City won the tie 3–1 after Peter Hart's back-pass to Cherry was held up in the snow 10 yards (9.1 m) short of the goalkeeper, leaving Paul Simpson to convert a simple chance to take the lead.
[22] Despite being injured with a sprained thumb he came on as a substitute in a youth team game against Derby County, playing outfield, and scored a headed goal past Mark Grew.
[22] Manager Dave Smith brought him in as a replacement for popular 34-year-old goalkeeper Geoff Crudgington, and gave Cherry his debut in a 1–0 defeat at Stoke City on 6 December.
[24] He enjoyed a good 1987–88 season and a much-improved relationship with the fans, being rewarded with the club's Player of the Year award with 34% of the vote, more than double the percentage received by second-placed Mark Smith.
[24] The club finally found their replacement by signing Rhys Wilmot from Arsenal, which allowed Cherry to join Chesterfield in the Third Division for a three-month loan period from January.
[29] On 16 February, he was described by reporter Sue Mott as being "all reflex and brilliance" as he kept a clean sheet in a 1–0 victory over top-flight Manchester City at Meadow Lane in the fifth round of the FA Cup.
[9] County lost 2–1 to Tottenham Hotspur in the following round, with Paul Gascoigne's winning goal described as "planted with such precision that even Cherry could do nothing about it" by BBC commentator John Motson.
[38][29] The 1991–92 season saw Cherry play top-flight football for the first time in 11 years, and he opened by the campaign by being named as man of the match in a 2–0 defeat to Manchester United at Old Trafford.
[29] Four days later he was named as man of the match in a 2–0 defeat to Arsenal at Highbury, having had to make four diving saves from Ian Wright whilst wearing a pair of gloves borrowed from opposition goalkeeper David Seaman following a mix-up before the game.
[39] On 10 March, he gave away a penalty, which he subsequently saved to earn another man of the match award, though the 0–0 home draw with Aston Villa left County in the relegation zone.
[29][40] Cherry was unhappy with his wage reduction and became unsettled early in the 1992–93 season, whilst key first-team players such as Tommy Johnson, Paul Rideout and Dave Regis were sold off to fund a £3.4 million redevelopment of Meadow Lane.
[29] County suffered a poor start to the 1993–94 campaign, losing 11–2 on aggregate to Newcastle United in the second round of the League Cup, with Andy Cole scoring a hat-trick in both legs.
[29] Howard Kendall replaced Slade as manager the following month and signed Australian goalkeeper Jason Kearton on loan from Everton to be the club's new number one.
[44][45] Cherry put in extra work in training to lose 11 pounds in weight and was rewarded with a place in the Anglo-Italian Cup final game with Ascoli at Wembley on 19 March.
[50][5][21] Cherry left Vicarage Road to return to former club Plymouth Argyle on a three-month loan starting in February, in a move that reunited him with former boss Neil Warnock.
[53][54][55] Cherry then moved on to Rotherham United, after being offered a two-year contract on £400-a-week (with a £20,000 signing-on fee) at Millmoor by management duo Archie Gemmill and John McGovern.
[49] He turned down an offer from Bolton Wanderers manager Colin Todd to be the club's third-choice goalkeeper and instead joined Kettering's Conference rivals Rushden & Diamonds in March 1997 on wages of £400-a-week, with a £20,000 signing-on fee.
[49] He played ten games for the Diamonds at the end of the 1996–97 season as the ambitious newly formed club began to build a strong squad under the ownership of Max Griggs.
[49][58] He played the opening game of the Third Division 1998–99 season for Mansfield Town on 9 August 1998, a 3–0 defeat at Brentford, as regular custodian Ian Bowling was unavailable and Steve Parkin needed a goalkeeper for the one match.
[59][60] He spent the 2003–04 season playing for Kidsgrove Athletic in the Northern Premier League Division One and helped the club to win their first Staffordshire Senior Cup with victory over Stafford Rangers in the final.
[49] In 2006 he returned to Notts County as a part-time goalkeeping coach, leaving when Ian McParland replaced Steve Thompson as manager the following year.
[65] The book was written by Jonathan Nicholas, who in his former career had patrolled around the Meadow Lane pitch as a policeman when Cherry played as a goalkeeper at Notts County.