A player with Bristol Rovers, and QPR amongst others, Holloway ended his playing career at his home town club Bristol Rovers and entered his first managerial job as player-manager of Rovers in 1996 guiding them to the play-offs in his second season.

Midway through the 2000-01 season 'Ollie as he is nicknamed was appointed manager at Queens Park Rangers where he was given the seemingly impossible task of keeping the now-struggling team in Division One. He failed to do so, as QPR finished second from bottom and were relegated to the third level for the first time in 34 years. Despite the relegation, Holloway stayed on and rebuilt the side. After steadying the ship in 2001-02, and a near miss in 2002-03, Holloway and QPR were promoted back to the second level in 2004, finishing second behind Plymouth Argyle a club who was later to manage.

Holloway's first full season in The Championship ended with a respectable 11th place, and during the following season 2005-06, the club continued to hover around mid-table, however in February 2006 things turned sour at Loftus Road and Holloway was placed on gardening leave, but in June 2006, Holloway was back in management this time at Home Park Plymouth.

During his stint at Home Park, Holloway took the Pilgrims to verge of the play-offs with some great attacking football, players like David Norris Akos Buzsaky, Peter Halmosi, Sylvan Ebanks-Blake and Dan Gosling all became targets for bigger clubs and eventually the money talked and Holloway's promotion chasing team was broken up and in November 2007 Holloway left Home Park and later accepted the manager's post at Leicester City where he became their 5^th manager of the season. He made history by winning his first game in charge against Bristol City but failed to turn the Foxes fortunes round and at the end of the season left the club by mutual consent.

Since then Holloway has been a regular on Sky Sports and Radio Five Live covering games up and down the country.

Away from football Holloway is married to his childhood sweetheart and they have four children William, twins Eve and Chloe, and Harriet. The twins were born profoundly deaf as was Harriet as a result Holloway has learned to communicate via sign language and has become a high-profile campaigner on deaf issues and concerns.