As a youth, Eastwood played in the 1979
Quebec International Pee-Wee Hockey Tournament with a
minor ice hockey team from South
Ottawa. Eastwood was drafted in the fifth Round, 91st overall by the
Toronto Maple Leafs in the
1987 NHL entry draft. He then played four seasons with
Western Michigan University of the
CCHA. He played 164 games for Western Michigan, scoring 69 goals and adding 80 assists for 149 points. His best season was his last one when he had 29 goals and 32 assists in 42 games. In 1991, Eastwood made the jump to pro hockey. He did not become an
NHL regular though until two years later. In 1995, Eastwood was traded to the
Winnipeg Jets for
Tie Domi. This started a trend for Eastwood as he would then go on to play for many different teams. In his career, he has played 783
NHL games, scoring 87 goals and adding 149 assists for 236 points. His best season came in
1999–2000, when he scored 19 goals and 15 assists for 34 points. ==Post-playing career==