He spent five years playing in the lower leagues, including spells at Heswall, Welsh sides Caernarfon Town and Newtown, and Runcorn.
Praised for his languid left foot, attacking flair, crossing and shooting ability, but questioned over his lack of pace, Woan established himself as one of the most prominent figures in the Forest team.
"[citation needed] Forest went on to win the replay at White Hart Lane 3–1 on penalties after a 1–1 draw, with Woan converting his spot kick.
Following manager Frank Clark's departure in December 1996, Woan's Forest career began to suffer although the winger was the only player to play for the Reds in each year of the 1990s.
Upon leaving Forest in 2000, and after a short trial with Bolton Wanderers, Woan signed for Swindon Town and in the 2000/01 season, producing three goals from 25 appearances.
Married to an American wife, the then 33-year-old winger endured a difficult season in Major League Soccer with the team winning just two of their eight opening matches.
Woan teamed up with ex-Forest striker Nigel Jemson and the pair notably inspired the Shrews to one of their greatest ever results.
The Shropshire outfit defeated Everton – who featured a young Wayne Rooney – in January 2003 in the third round of the FA Cup, with Jemson scoring twice.
It was Woan's last minute cross that ensured the Premier League side's fate, but the Shrews were knocked out of the competition 4–0 by Chelsea the next round in a televised match.
Woan then joined the Syracuse Salty Dogs of the A-League (the U.S. second tier) and competed in another season in the States before deciding to return to England.
Woan headed back to Swindon Town, taking charge of the under 18 side at the County Ground until deciding to move to Rushden & Diamonds as first team coach for Paul Hart in July 2006.