Winchester made his NHL debut with Ottawa in the 2007–08 season, playing in a single game against the Boston Bruins on March 29, 2008, registering no points and two penalty minutes.

[4] After scoring 10 points in 11 games and with limited NHL interest, Winchester opted to remain in Finland and was elevated to the SM-liiga club, Jokerit for the remainder of the 2012–13 season on January 27, 2013.

[9] Winchester suffered a setback after training with the club, and was effectively ruled out from the remainder of the season preventing him from making his Avalanche debut.

[10] However upon resumption of full training, Winchester's concussion symptoms flared up prior to pre-season games and he was again placed on the injury reserve, ruled out indefinitely.

By November, Winchester had left the team and returned home to continue his recovery effectively marking the end of his tenure without ever appearing with the Avalanche.