Booker was initially spotted by Watford whilst playing for Saturday side Bedmond Social and they invited him to attend a couple of training sessions before he also caught the eye of Brentford and was offered a trial. Despite being a midfielder he was played as a striker in his trial game and duly scored two goals prompting Brentford to offer him a deal. After agreeing a 'fee' with Bedmond, which saw the non-league side receive a set of tracksuits, Booker signed for the Bees and made his Football League debut two days later on 14 October 1978, ironically against his home-town club of Watford.
After a short loan to Conference side Barnet where he netted a couple of goals, he returned to Brentford and duly scored a hat-trick in his first game back. From this point he became a stalwart of the Brentford first team and would be virtually ever present for the next ten seasons at Griffin Park eventually making over 250 appearances for the Bees. Noted for his versatility, by the time Booker was voted the Bees Player of the Season in 1982 he had played in every position apart from goalkeeper.
Booker's time at Brentford was marred when he suffered a cruciate ligament injury in 1986 which kept him out of the side for nearly eighteen months with the surgeons claiming he would never be able to play again. He returned to fitness and played a few first team games but was now deemed surplus to requirements and offered a testimonial game and a free transfer.
Booker was considering quitting football, taking the money from the benefit game that Brentford had offered him and putting the money into a window cleaning business. His final contract with Brentford had given him the option of a free transfer should he choose it, in recognition of ten years good service to the club, but it was still something of a surprise when Dave Bassett offered him the chance to move to Sheffield United in 1988 having monitored his progress for a number of years. Blades midfielder Simon Webster had broken his leg and United needed someone to replace him so club physio Derek French, who had played with Booker back in his Bedmond days, contacted him to see if he was interested in a move North. Within 24 hours Booker had signed for the Blades.
Over thirty years old, with a recurring knee injury and seemingly with his best years behind him Booker proved an inspired signing, as he became the linchpin of the side that rose through the divisions to reach the top flight in 1990. A cult hero with the Bramall Lane fans Booker endeared himself with his gutsy performances and genuine affection for the club and its fans who he would happily spend hours chatting with. On one occasion a ten-year-old fan wrote to the club asking if Booker could come to dinner at his house – a request which he duly obliged, staying for two hours and eating a hearty meal!
Booker continued to be a key player in Division One before injuries finally started to take their toll and he was allowed to return to Brentford in 1991.
Signing a three-year deal with The Bees, nearly five years after they had deemed him surplus to requirements, Booker suffered a difficult return. A squad player he was part of the side that were crowned Division Three champions in 1992 but then suffered an immediate relegation the following year. Booker's knee problems had returned as well, and he was forced to retire in 1993 on his doctor's advice. Booker was inducted into the Brentford Hall of Fame in November 2014.
After drifting out of football for a while Booker eventually took up a coaching post at Brentford in 1994 before being offered the position of assistant manager to Micky Adams at Brighton & Hove Albion in 2000. When Adams left after the side were promoted Booker was made joint caretaker manager along with Martin Hinshelwood before the arrival of Steve Coppell. Remaining at the club he was again called upon to act as caretaker manager in 2003 after Coppell quit to join Reading. New manager Mark McGhee retained Booker as his assistant and the pair remained in charge until McGhee was sacked following a poor start to the 2006–07 season. After a spell managing village side Pease Pottage FC Booker returned to Brighton along with Micky Adams in 2008 to take up the position of reserve team coach.
Booker now works as a driving instructor and summariser on Brighton & Hove Albion's match commentary.Brentford Player of the Season: 1981/82
Brentford Hall Of Fame
Football League Trophy
Runners-up – 1988/89
Booker left school at 16 to begin a four-year apprenticeship in an upholstery warehouse whilst playing Saturday football. During his first game for Brentford he was marked by Watford defender Ian Bolton who would eventually join him at Brentford and ironically end up as his brother-in-law.
Following his retirement from playing Booker made occasional appearances as match summariser on BBC Radio Sheffield and married former Southern FM breakfast show host Nicky Keig-Shevlin in 2008.
In July 2017, a biographical book of Booker’s life, written with his support, was published. OOH-AAH: The Bob Booker Story ISBN 978-1910515594.