On leaving school in May 1969, Little signed for Aston Villa who would be relegated to the Third Division for the first and only time in their history in the following season. He played a full season for the Aston Villa Youth side and subsequently made his senior debut on 30 October 1971, in a 4–1 win over Blackburn Rovers in the Third Division at Villa Park. He only made two senior appearances that season but was a key player in Villa’s FA Youth Cup winning side of 1972. By 1973–74, with Villa in the Second Division, he was a regular first team player. He made 247 appearances for the club and scored 60 goals, and made one full international appearance for England in 1975.

He was part of Villa’s League Cup winning teams of 1975 and 1977, scoring two goals in the second replay victory over Everton in the latter final, as well as helping the club climb from the Third to First Division in the early part of the decade, scoring 20 league goals in the 1974–75 season when they were runners-up and clinched promotion to the First Division. His playing career came to a halt in 1980 when he retired at the age of 26 due to a knee injury.

Brian Little was appointed caretaker manager of Wolverhampton Wanderers on 31 August 1986 as successor to Sammy Chapman. His appointment came at the end of the blackest spell in the club’s history, when three successive relegations had dragged them from the First Division to the Fourth. He oversaw a steady start to the 1986–87 season before Graham Turner was appointed manager 36 days later.

By this time, bigger clubs were taking an interest in the 37-year-old Little and in June 1991 Leicester City appointed Little as their replacement for Gordon Lee. The Foxes had just avoided relegation to the Third Division for the first time in their history and Little was seen as the right man to turn the club’s fortunes around.

In 1993–94, however, Leicester won their third consecutive play-offs with a 2–1 win in the final against East Midlands rivals Derby County. In November 1994 Little returned to Aston Villa to replace Ron Atkinson. Leicester’s first Premier League season was a difficult one and they were relegated in second from bottom place, with just six league wins all season. Earlier in the year, former Middlesbrough youth coach Little had been linked with a return to the Teesside club as manager following the departure of Lennie Lawrence, but the job went to Bryan Robson instead.

Villa qualified for the 1996–97 UEFA Cup and although they were knocked out at the first stage by Swedish side Helsingborg, they qualified for the 1997–98 competition after finishing fifth in the Premiership. In February 1998, Little resigned after just over three years as Aston Villa manager, with the club in the bottom half of the Premiership, the club’s next manager John Gregory turning results around. They finished the season high enough for a UEFA Cup place.

Little was appointed manager of Stoke City in May 1998 and his appointment was met with approval from the club’s supporters. Stoke in 1997–98 had moved from the Victoria Ground to the new all-seater Britannia Stadium but poor performances led to the side being relegated to the Second Division. Little arrived with the only objective was to gain an instant return to the First Division in 1998–99. Stoke began the season in fine form winning 14 of their first 20 matches and they sat well on top of the division. However their form completely fell away after Christmas and won just seven matches from the remaining 26 and ended up finishing in 8th position. One of those defeats was a 2–0 loss against nine-men Millwall, which Little described as “the worst result in my twelve years in management”. In July 1999 Little resigned and stated: “I have tried my best and the disappointment is very hard to take. I hope the supporters understand that it’s best that I leave”.

In January 2000 the promising Italian midfielder Enzo Maresca was transferred to Juventus for £4 million as Albion battled against relegation. Little was sacked in March 2000 after just eight months in charge and replaced by Gary Megson.

In April 2000, just one month after leaving the Hawthorns, Little was appointed manager of Division Three strugglers Hull City. The Tigers were hit by huge debts and were locked out of Boothferry Park for one game by the landlord, former tennis player David Lloyd. By the end of the 2000–01 season, Hull had been saved from closure by new owner Adam Pearson, and the club’s future looked brighter. They reached the Division Three playoffs, but lost to Leyton Orient in the semi-finals.

In autumn 2001, following the dismissal of manager Peter Taylor, media reports suggested that Little was going to be approached by Leicester City about a possible second spell as manager, but the job went to Dave Bassett instead. By February 2002 Hull City looked well on course for automatic promotion from Division Three. But Little unexpectedly announced his resignation from the club, and under his successor Jan Mølby, the club’s fortunes slipped dramatically and they could not even finish high enough for a play-off place.

In October 2003, Little made a return to football management with Tranmere Rovers, who were in Division Two.

Tranmere began 2005–06 as League One promotion favourites, but at the turn of 2006 they were facing a relegation battle. The club only avoided relegation with one game to go and, due to the club’s poor finishing position in League One, he left the club by mutual consent on 5 May 2006.

The injury was discovered when Little was undergoing a medical at Villa’s local rivals Birmingham City. This meant his intended transfer there was cancelled. He was a flamboyant forward who formed a particularly prolific partnership with Andy Gray. Little is regarded as an all-time great at Villa Park, and in 2007 he was named as one of the 12 founder members of the Aston Villa Hall of Fame.

Out-of-work Little was linked with a return to management with both Gillingham and Port Vale. However, in November 2007, Little took the reins at Wrexham, replacing Brian Carey. With five games remaining in the season the club were in the relegation zone, seven points off safety. They were relegated to the Conference on 22 April 2008 after a 2–0 loss at Hereford United. However, Little signed a two-year contract, promising to revive the club’s fortunes.

On 28 August 2009, Little was appointed manager of Conference North side Gainsborough Trinity. The club had moved to appoint him following the recent dismissal of manager Steve Charles and the resignation of his coaching staff which included formerly appointed caretaker managers Dave Reeves and Steve Blatherwick. However, Little would not take charge of the club’s away fixture the following day against Farsley Celtic after it was announced he would not take over from player/caretaker manager Adie Moses until 7 September. Little began building a squad of professionals at Trinity, picking up many players from the Football League and other ex-League players from the Conference National, but despite boasting a large squad of experienced players Trinity narrowly avoided relegation to the Northern Premier League during the 2010–11 season. On 22 August 2011 following one win and two defeats in the opening weeks of the 2011–12 season, Little was sacked as manager of Trinity with Steve Housham taking over as caretaker manager.

Little was appointed as the Jersey FA’s Director of Football in November 2014, overseeing the work of first team manager Jimmy Reilly. Reilly went on to lead the islanders to their first Muratti Vase Final victory in four years the following May. Months later, Jersey announced their intention to join UEFA, and when Reilly stepped aside in early 2016 Little was appointed to replace him.

Little won the Muratti in May 2016, but stepped down as manager the following month and reverted to his position as Director of Football; allowing him to concentrate on his commitments at Aston Villa.