Tottenham's Irish Under 21 striker Neale Fenn joined Norwich on loan on transfer deadline day in March 1998. He made a total of seven appearances for the Canaries, scoring once in the 5-0 thrashing of Swindon on April 25th 1998. In addition to his appearances with Norwich, Neale spent an earlier part of the 1997/98 season on loan to Leyton Orient. A third loan spell occurred in Neale's career in November 1998 when George Graham allowed him to join Swindon Town for whom he made his debut on 14th November against Bradford in a 3-0 away defeat. A fourth session saw him join Lincoln City on loan later in 1998/99.

On 7th March 2000, Tottenham announced that six of their squad were up for sale including Fenn and Ruel Fox. The Football Transfer website reported on 26th June 2000 that Neale was being lined up for a £350,000 move across London to ambitious Brentford. However an "unnamed Dutch side" were also believed to have made an offer. Neale didn't depart from White Hart Lane as expected until over a year later. He had a trial with Peterborough in April 2001. Scoring regularly for the Reserves during his trial (including 2 vs Wycombe on 2nd May), Barry Fry signed Neale on a 12month contract via a free transfer on 3rd May 2001.

In early June 2003, Neale was linked with a return to North London as part of the transfer deal that would take Barnet striker Junior Agogo to Peterborough. He was also linked with Dagenham & Redbridge. Neale had made just 8 starts during the 2002/03 season. As a result, his contract was cancelled with mutual consent in late June 2003.

The following week saw him join Dagenham for pre-season training. When the Daggers decided instead to opt for new strikers Alex Meechan and Keith Scott, Neale then joined Stevenage Borough on trial. He played for Boro against Potters Bar and Peterborough, the former game seeing Scott Howie also trial for Stevenage. On 21st August 2003, Neale abandoned English football and signed for Eircom League side Waterford United. He transferred to Cork City in December 2003. He has became a crucial part of the team and was a near ever-present in Cork Citys successful league title campaign of 2005. He is now settled in Cork with his wife and baby girl and operates a fashion store Indigo in the City Centre with team-mate Joe Gamble.

Neale joined Bohemians after his contract with Cork City F.C. expired in November 2006. Fenn got the only goal of Bohemians' opening game in the 2008 Eircom League as they defeated Galway United 1-0 on 8th March 2008.

Neale moved to Dundalk in January 2010

On July 29th 2010, he announced his retirement from football with immediate effect due to personal reasons. Fenn insisted he would not be making a return to football. “I think once you finish you might as well finish rather than making all sorts of comebacks. At the moment, I can’t see myself coming back at all.” However, only four days later on 3rd August 2010 Fenn signed for Shamrock Rovers until the end of the 2010 season.

In 2011, he joined Swords Celtic of the Leinster Senior League.

In April 2017 he was appointed Assistant Manager of Leyton Orient until the end of the 2016/17 season. On 27th June 2017 he was appointed manager of Longford Town in the Irish first division.

In August 2019, he was appointed manager of Cork City. On 7th October 2020 Fenn stood down as Cork's manager with the club bottom of the table with four games left in the season