Woosnam played football with Montgomeryshire Schoolboys and gained youth international honours with Wales, and gained eight amateur
caps, the first against England in 1951. While studying
physics, he captained
Bangor University's football team at the Welsh Universities' Championship and played for the Peritus club. Woosnam completed his national service with the
Royal Artillery where he played for 55th RA Tonfanau and was selected for the Army XI several times, including alongside
Eddie Colman and
Duncan Edwards of
Manchester United. Retaining his amateur status throughout, Woosnam played club football for
Welshpool,
Oswestry Town,
Bangor City,
Wrexham,
Wolverhampton Wanderers,
Manchester City,
Caersws,
Aberystwyth Town,
Portmadoc,
Sutton United, as well as guesting occasionally for
Middlesex Wanderers, before he joined
Leyton Orient. His only Manchester City appearance was in a 6-0 defeat versus Cardiff City at Ninian Park. He made his senior international debut for
Wales against
Scotland in October 1958, having turned professional in January 1957. He represented the
London XI against
Lausanne Sports while at
Brisbane Road. He was named amateur footballer of the year in 1955. A condition of his release from teaching to turn professional with the Hammers was that the Upton Park club would send its first team to face the school's first XI. Such a fixture became a regular annual occurrence at Leyton County with West Ham visiting again - once with Woosnam as Hammers' captain - as well as Charlton Athletic, Leyton Orient and Crystal Palace. While at Leyton County Woosnam would recommend promising schoolboys to Leyton Orient. He made his debut against
Arsenal that month and went on to make 138 league appearances for the club, scoring 26 goals. He made 15 cup appearances, scoring three goals. While at
Upton Park, he added 14 full international caps to the one he had gained while at Orient. He also represented the
Football League and the
Wales national amateur football team, for whom he won 16 caps, scoring four goals, only one less than the national amateur record. His caps total places him joint 7th in the all-time amateur appearance list. Woosnam moved to
Aston Villa in 1962 for a £25,000 fee. He made his Villa debut on 1 December 1962 in a 5–0 home win against
Bolton Wanderers. He went on to score 24 goals in 106 League games, and gained a further two international caps. ==Coaching career==