A stylish inside-forward, Charlie Rackstraw graduated from the side that lost to Manchester United in the 1956 F.A. Youth Cup final and came into the first team as it declined from holding a regular position among the leaders in the Third (North) to scrapping it out, down among the dead men in division four. This fact in no way reflects on his ability, though. Like many gifted Chesterfield players, he had occasional brushes with the management, and fans came to feel that his face didn't fit at the club.

One occasion that seemed to typify Charlie's treatment occurred in March '61. Held up by a delayed train at Sheffield station, Charlie arrived in time to make the team against Hull City, but late for the "call." He was dropped. (His replacement, Gwyn Lewis, was plunged into the first team for the first time in ages, had a stinker and was booed off.) He had to deal with frequent accusations of laziness and his commitment was often called into question - although not after an infamous game at Doncaster in April '62, when he was punched to the floor by Rovers' Tony Leighton when the final whistle blew on a 3-0 win for Chesterfield.

He formed an effective partnership with Keith Havenhand and, upon that player's sale, took on the mantle of goalscorer, topping the club's scoring charts in '62-3 and '63-4. The club apparently turned down an offer of £10,000 from Luton for him in March '63. A year later, Chesterfield accepted less than half that from Gillingham in a deal that brought the ill-fated Peter Stringfellow to the Rec. He found greater appreciation at Priestfield and, particularly, at Bradford City, who he helped to promotion from the Fourth in '68-9.He is reputed to have had a 100% success record from the penalty spot. After football, Charlie became an insurance broker.

For Chesterfield: 172 FL appearances, 48 goals.