Keogh’s first association with Leeds was as a trainee from July 2003 until February 2005. Despite being at Elland Road for nearly two seasons, he made only a solitary senior appearance, coming in a League Cup-tie — he never featured in a league match for the club during that spell. His limited opportunities led to several loan moves — initially to Scunthorpe United in League Two, where he scored twice in 12 appearances, and later to Bury, where he added four appearances and two goals before permanently transferring to Scunthorpe in February 2005 for around £50,000.

At Scunthorpe, Keogh found his groove. During the 2005/06 season, he played 45 league matches and scored 11 goals, helping establish himself as a reliable striker at that level. His performances drew interest from higher-division clubs. By January 2007 he had been signed by Wolves for approximately £600,000 — returning to his parent club after initially developing in their youth ranks.

At Wolves, Keogh’s career gathered momentum. He made 17 league appearances and scored five goals in the 2006/07 season as Wolves pushed for promotion. Over the next two years he featured regularly in the Championship, including 43 league games in 2007/08 with eight goals, and 42 appearances in 2008/09 with five goals. Following Wolves’ eventual return to the Premier League, his playing time there diminished sharply — just one league appearance in 2009/10 and none the following season.

By August 2011, Leeds United once again came calling. Simon Grayson brought him in to plug the gaps left by injuries to Luciano Becchio, Davide Somma and Billy Paynter. Grayson told the club's official website, 'Andy will strengthen our striking options. He's got plenty of experience, having played a lot at this level and in the Premier League. He's also returning to the club where he started his career so he knows what it's like here and understands the place.'

Keogh expressed a desire to resolve 'unfinished business' at Elland Road after his first stint yielded minimal action.

His second spell at Leeds proved far more impactful. He made 22 league appearances, scoring two goals, and added a couple more outings in Cup competitions during the remainder of the 2011/12 season. He debuted on 16 August in a commanding 4–1 victory away at Hull City, often partnering or rotating with Ross McCormack as part of Leeds’ frontline. His first goal came in a lively 3–3 draw against Brighton & Hove Albion in September, with additional contributions coming during a campaign where goals were at a premium for Leeds.

During that season, Leeds underwhelmed — finishing 14th in the Championship and undergoing managerial upheaval, from Grayson to caretaker Neil Redfearn and Neil Warnock from February. Despite the instability, Keogh’s presence brought physicality, work rate, and experience up front. He also occasionally operated from the left flank — a sign of his adapting willingness when team structures shifted.

Off-field, fans admired Keogh’s commitment and attitude. As Luciano Becchio returned from injury and regained form, Keogh's playing time was gradually reduced. In January 2012, the loan ended early; Leeds declined to make the move permanent, and he returned to Wolves before being immediately transferred to Millwall on the same day the loan expired.

At Millwall, Keogh revitalised his career. In the remainder of the 2011/12 season, he scored 10 league goals, finishing as the club’s second-top scorer behind Darius Henderson, and provided leadership in a squad featuring emerging talents like Harry Kane on loan. That form earned him a permanent contract extending beyond the campaign.

Beyond these Leeds chapters, Keogh enjoyed a well-travelled and varied career: loans to Cardiff City and Bristol City, Premier League action with Wolves (13 appearances, one goal), and moves abroad later in his career to Perth Glory in Australia's A-League and Ratchaburi in Thailand, plus a stint at NorthEast United in India before returning again to Perth Glory and continuing into the early 2020s.

Internationally, Keogh represented the Republic of Ireland, earning over a dozen senior caps between 2007 and 2012 and scoring in friendly and qualifying matches. Known for his physical presence, intelligent movement, and aerial threat, he suited the prototype of a traditional centre-forward who combined work-rate and instinct.

Reflecting on Keogh’s dual Leeds spells: his initial 2003–05 stint was largely hidden in the youth/reserve setup with no league minutes, a frustrating introduction at a time when Leeds were struggling financially and managerial decisions were inconsistent. His second spell seven years later was markedly different — he became part of the senior squad, scored key goals, and helped bring stability to a squad in transition under Grayson and Warnock. That contrast across the two spells illustrates the unpredictability and contingency in football careers.

His outgoing moves post-Leeds were characterised by resurgence — especially at Millwall and then Perth Glory, where he became a fan favourite. Internet threads among Perth Glory fans frequently hailed him as a club legend, citing consistent performance and community engagement well into his thirties.

By the time of his retirement announcement in April 2022, Keogh had amassed around 381 senior league appearances and 118 goals across all clubs Soccerbase . He had played in multiple countries and levels — from top-level Championship and Premier League to A-League and Indian Super League. His legacy is one of persistence, versatility, and professionalism.