The Irishman started his career as a trainee at Charlton Athletic in 2000, eventually leaving five and a half years later without making a single appearance for the Addicks.|
At 16-years old, Neil was called into Charltonâ€™s first team squad to face Manchester United. The midfielder also represented the Republic of Ireland at youth levels from Under-16 through to Under-19.
During his time at The Valley, he was a regular in the Under-19â€™s and Reserve team, later captaining the Reserves in 2004/05.
Whilst at Charlton, Neil also had loan spells at Cambridge United and Rushden & Diamonds â€“ both when they were Football League clubs. He made six appearances whilst on loan with Cambridge and 16 in his first spell with Rushden & Diamonds.
McCafferty went on to sign for The Diamonds on a permanent deal after impressing whilst with the club where he was on loan the previous season. He made a further three FA Cup, one League Cup and two Football League Trophy appearances on top of 23 League Two caps. During his spell in English football, Neil failed to hit the net.
In July 2006, McCafferty signed for his hometown club Derry City. Stephen Kenny persuaded Neil and a few other Irish players based in England to rekindle their career back home across the Irish Sea in the Eircom Premier League.
However Neil only managed to make a handful of appearances for Derry picking up a red card along the way.
In November 2007, the 23-year old went on trial with former Grays Ath boss Mark Stimson at League One club Gillingham, playing in a friendly against Dagenham & Redbridge.