Chilton arrived at the Tigers as a raw youngster who had stood the buffeting of local non-League football and still managed to score goals. Yet if he had gone to Art College, as originally intended, he may never have worn the Black and Amber at all. Fortunately fate steered him in the right direction and Chilton gave over 10 years loyal service to the club and much heartache and happiness to defenders and supporters respectively. His League debut was not the most auspicious of occasions, the Tigers lost 4-0 to Colchester and in that game he wasn't even first choice as centre-forward. That honour went to another debutant, Peter Nicholson - who never played another first team game for the Tigers - whilst Chilton went on to make the number 9 shirt his own in 477 League and Cup games.
In the early days Chilton's rawness was evident but his prowess in the air and in front of goal was awesome. His first full season saw him play in 50 League and Cup matches with 20 goals (including a hat-trick) to his credit. He learnt well from seasoned pro's such as Jackie Sewell, Ralph Gubbins, Eric McMillan and Doug Clarke. His second season was not so fruitful but as each subsequent season passed, the rawness became the finished article and he built up a reputation as a willing worker for the team but with the individual talent to score goals. Season 62/63 saw him score two of what would turn out to be 12 career hat-tricks. In the following season he went one better scoring 4 goals in the League game against Wrexham (a feat he would repeat a year later, this time in the 7-0 thrashing of Barnsley, for completeness the other three goals were scored by Ray Henderson). The name Chris Chilton was no longer necessary to identify this goal machine, 'Chillo' would do.
As his reputation grew so did the attention. And not all of it was welcome. His ability to average nearly a goal every other game made him a marked man. On occasions it was literally so as defenders grew desperate in trying to deal with this giant. He could look after himself there was no doubt and, as insurance, he always had Andy Davidson as his guardian angel, often taking the opportunity to have a word with the offending individual when the Referee's attention was diverted. Help would be at hand from another quarter as well for shortly after his 'Barnsley Quartet' Ken Wagstaff would join him. 'Waggy' would create his own niche in the history of the Tigers as a goal scorer par excellence but in tandem with Chilton they would form probably the most devastating strike partnership the club and its supporters had ever seen. In the remaining 26 games of that 64/65 season after Waggy signed from Mansfield, he and 'Chillo' scored 38 goals between them as the Tigers came close to promotion. In the following season they scored 27 and 25 goals respectively as City stormed to the Div. 3 championship and gained national recognition for their FA Cup exploits.
The remainder of Chilton's career with the Tigers was played out in Division 2, the occasional flirtation with promotion being generated by his and Waggy's ability to score goals aplenty but often scuppered by the defence's ability to be equally as generous. During this time Chilton gained his first representative honour, when selected to captain an F.A. XI against Guernsey. He marked the occasion by scoring a hat-trick and would play for the FA some three years later but such recognition was a scant reflection on his ability; he deserved better but never complained when he didn't receive it. By the end of the 60's Chilton was still scoring regularly but not with the same profligacy as injuries were beginning to take their toll and his absences as a result grew in frequency. He still had it in him however to score his twelfth career hat trick during the 70/71 season against Sunderland, a game televised so that millions could enjoy the masters at work as Messrs. Chilton and Wagstaff destroyed Sunderland 4-0. It would be his last hat-trick and came during a spell of nine matches in which 'Chillo' scored 11 times. Early into the start of the 71/72 season he finally got his chance in the top flight, joining Coventry for a fee of just over £90,000. It would prove, in hindsight, to be good business for he only played a single season for them before a recurring back injury forced him to retire. At least it spared the City faithful from having to watch the footballing end of a legend.
His association with the Club would not be broken for long however and in the 70's and 80's Chilton carried out a number of coaching and caretaker manager duties with his beloved City. He worked well with the players and was responsible for turning Billy Whitehurst into a goalscorer of some quality, if not with the same durability as Chilton.