Born in Brighton, England, Ifill was in part of Watford's youth programme but was not offered a professional contract and moved to non-league Saltdean United.

Fortunately, a Harley Street consultant diagnosed a pelvic flaw pressing on a nerve, and the day after treatment he was able to sprint again [citation needed].

In his first season at Bramall Lane, United raced into a large lead, and despite falling behind eventual champions Reading, the Blades finished as runners-up, securing promotion to the Premier League in the process.

During the January transfer window, Ifill left the Blades and after much competition from other clubs was unveiled by Crystal Palace, having signed for a reported £800,000 fee.

He scored his first goal for his new club in his second appearance netting a header off a pinpoint cross from Leo Bertos to help secure a 2–1 win over Perth Glory at Westpac Stadium.

On 6 September 2009 two days after his goal against Adelaide, Ifill signed a contract extension to keep him at the Phoenix until the end of the 2011–12 season, with an option for an extra year.

On 31 December 2009, Ifill scored both goals in a 2–0 win over the Central Coast Mariners, pushing the Phoenix back up to seventh position in a congested ladder.

Ifill then scored twice more against Central Coast Mariners in the final round of the regular season to help his team to a 3–0 win, securing fourth position.

In the process, Ifill joined former Phoenix marksman Shane Smeltz as record holder of most goals scored in a regular season (12).

Ifill stepped down from Christchurch United at the end of the season and moved to become the Director of Football (DoF) at Wellington Olympic.

On 24 September 2006, he scored a hat-trick for Barbados during their 7–1 Gold Cup qualifying victory over Anguilla at the Antigua Recreation Ground.

Ifill was recalled for Barbados' semifinal Group G, in which he scored twice in three games, as the hosts advanced to the finals, in Trinidad and Tobago, in January 2007.