Stephen joined Luton as a 13-year-old, when he was spotted playing for Barnet Schools. He made a big impression as a Schoolboy playing in the U-19 Youth Alliance side in the 2000-01 season - scoring on his full debut at Barnet, and going on to play almost a full season, netting five goals in 28 appearances. He was awarded a Scholarship during the 2001-02 summer along with fellow Centre of Excellence boys Kevin Foley and Parys Okai, and Luton fought off competition from top London clubs for his signature.

A regular for the reserve and U-19 sides during the 2002-03 season, Stephen failed to make a first-team appearance during the season, but he went on to enjoy success at senior level during the 2003-04 campaign under new boss Mike Newell.

Able to operate anywhere across the midfield, although more comfortable in the centre, Stephen made his senior debut in a 2-1 LDV Vans Trophy win at Rushden & Diamonds in early November 2003. In February 2004, he began to establish himself as a regular member of the first-team squad and he went on to make a total of 6 League appearances (3 as a substitute) after making his League debut as a late substitute in a 4-1 home win over Brentford in February 2004. He also netted his first goal at senior level in a 3-2 home victory over Sheffield Wednesday in the final home game of the 2003-04 campaign.

Stephen has an excellent 2004-05 season as he continued his progress with the Hatters and, in only his second season as a professional footballer, celebrated by helping Luton Town to the League One Championship, as they amassed a mammoth 98 points and returned to the Championship after a ten year absence.

After impressing manager Mike Newell during the pre-season friendlies, Stephen appeared on the right-hand side of midfield in the opening three League One matches, as the Hatters made a 100% start to the season by defeating Oldham Athletic, Swindon Town and Barnsley.

However, he was then dislodged from the side by the impressive and ever-improving Ahmet Brkovic, who remained on the right-wing for the Hatters thereafter, scoring 15 goals and playing an integral part of Luton’s successful season.

That didn’t, nevertheless, stop Stephen from appearing in the first-team on a number of occasions as he made appearances in the LDV Vans Trophy and the FA Cup. Mainly used as a substitute, Stephen made a further 14 League appearances during the campaign and he scored his only goal of the season – and his second goal at senior level during his career – in a 5-1 home win over Wrexham in early November 2004.

A Republic of Ireland U-19 international, Stephen appeared regularly for the Hatters’ Reserve side during the season as well, helping them to the Pontins Holiday Combination Cup and the South East Pontins Holiday Combination League Championship.

Unable to break into the Luton Town first-team squad during the 2005-06 season, Stephen made a loan move to League One outfit Tranmere Rovers where he gave an excellent account of himself and was a popular figure amongst the Tranmere supporters.

The young Irish midfield playmaker was so good in fact, that many Tranmere fans called for manager Brian Little to sign him on a permanent basis. However, it looks extremely unlikely that he will be allowed to leave Kenilworth Road with manager Mike Newell adamant that he has a bright future ahead of him.

Surprisingly sent off towards the end of his loan spell at Prenton Park, Stephen enjoyed making forward runs into the box and he returned to Kenilworth Road, signing a new one-year deal with the Hatters.

Very much a bit-part player for Luton Town in 2006-07, Stephen was a regular for the Hatters reserve side, but failed to force his way into manager Mike Newell's first-team on a regular basis.

However, following Newell's sacking and the arrival of Kevin Blackwell as manager, Stephen was handed a chance in the side and he ended the season in Blackwell's team as Luton were relegated from the Championship.

He was handed a new one-year contract by Blackwell during the summer.

Stephen had a solid if unspectacular season for Luton Town during the 2007-08 campaign - a season that was arguably the worst in the Hatters' history.

One of only a handful of players to emerge from a woeful season with any credit, Stephen didn't feature in the first-team squad under manager Kevin Blackwell and, although he was given a place on the substitutes bench on various occasions (making a rare outing as a late substitute at Premiership giants Liverpool in a televised FA Cup Third Round replay), he remained a squad member rather than a first-team regular. However, following the departure of Blackwell in January 2008, Stephen became a regular in the centre of Luton's midfield under new boss Mick Harford.

With the Hatters in administration and already deducted 10 League points as a result of this administration, Harford was unable to sign any new players. With a depleted squad, and Luton heading for relegation to League Two, Harford chose to utilise his small squad to it's full capacity and gave every player an opportunity to show what he could do, including Stephen.

Making a total of 16 League appearances during the season (6 as a substitute), Stephen, as always, looked a neat and tidy player in possession of the ball, going about his job quietly. It could be argued that this is his main fault and that he needs to get more involved and have more of an impact on matches if he's to truly realise his full potential.

One of a number of players out-of-contract at the end of the season, Stehen appeared regularly for Luton Town during the pre-season period prior to the start of the 2008-09 season, but he decided to reject the offer of a new deal with the Hatters - on reduced wages - and began the search for a new club after 45 League appearances and 3 goals for Luton Town.

In late August 2008, Stephen found a new club, signing a one-year deal with Hereford United.