Tuddenham made his VFL debut in
1962 against at
Arden Street Oval. His brand of football was fearless and tough, with a habit of grasping the football to his chest with his elbows sticking out dangerously. In recognition of his toughness and skills, Tuddenham was appointed Collingwood captain in
1966. In the semi-final against , he kicked seven goals on
Daryl Griffiths in a tense 10-point win to advance to the grand final. But St Kilda reversed the result two weeks later to take out the
1966 VFL grand final by one point, winning their first and only premiership so far. Collingwood were eliminated from the
1967 finals by eventual runner-up in the first semi-final. The Magpies trailed by one point at three-quarter time, but the Cats kicked six goals to one in the final quarter to win by 30 points. Tuddenham was reported for striking Geelong defender
Geoff Ainsworth on the head with his forearm in the last quarter by field umpire
Jeff Crouch. He was found guilty and suspended for four matches. In February 1970, Tuddenham and his deputy
Len Thompson were involved in a pay dispute after they learned that Collingwood had recruited its first interstate player,
Peter Eakins, from Western Australian club for a sign-on fee of
A$5,000 and A$5,000 a season for three years. That was A$2,000 more than Tuddenham was receiving as captain. Tuddenham asked for A$8,000 over three seasons, and Thompson A$30,000 over five seasons, threatening to walk out if their demands were not met. Three weeks later, during which time there had been no negotiations, both players returned. Although their demands had not been met they did obtain a slightly improved salary; under the clubs terms, Tuddenham would receive A$125 per match plus VFL provident fund payments, and Thompson would earn A$105 per match. Although Tuddenham was confident the little episode would not affect his chances of retaining the captaincy, the Magpies committee announced
Terry Waters as captain for the
1970 VFL season and Tuddenham accepted the decision. Collingwood finished on top of the ladder with 18 wins and defeated arch-rivals in a semi-final by 10 points to advance to the grand final. However, as had happened four years earlier against St Kilda, Carlton would reverse the result in the
1970 VFL grand final, coming from 44 points down at half-time to overrun Collingwood in the second half. Tuddenham was regarded among Collingwood's best players on the day. During the game he accidentally floored teammate
Peter McKenna in the second quarter with a hip-and-shoulder bump meant for a Carlton player. McKenna had kicked five goals up to that stage of the game and would only add one more for the rest of the match. In an interview 40 years later, Tuddenham cited a lack of fitness, as well as inaccurate kicking for goal, as the main reason Collingwood lost: "I suggested to (coach)
Bob Rose after we lost the
1966 Grand Final to St Kilda by a point that he do the coaching and I look after the fitness along with my friend John Toleman. The idea was that I would be an assistant coach, and I'll tell you what, I would have got the buggers fit." In
1971, Tuddenham became the first player to be named captain of the
VFL representative team whilst not captain of his own club. When asked about this, state coach
Tom Hafey replied bluntly: "We are not here to talk about Collingwood's mistakes." ==Post-football career==