In his first season with the Leafs in 1998-99, Cujo played 67 games, leading the Maple Leafs to the Eastern Conference Finals, losing to the Buffalo Sabres in five games. The following year, Joseph had another solid season going 36-20-7. He was selected to the all-star team that year, but once again, he and the Leafs would fall short in the postseason, this time in the second round of the playoffs to the New Jersey Devils.
During his next two seasons with the Leafs, Cujo experienced continued success. In 2002 he won a Gold Medal at the Olympics with Team Canada in Salt Lake City. Cujo again led the Leafs to the Eastern Conference Finals, but lost to the Carolina Hurricanes in a heartbreaker. Joseph left the Maple Leafs in 2002 to sign with the Detroit Red Wings after rumours of friction between him and Pat Quinn surfaced. Joseph's exit to Detroit was bittersweet. As he mentioned in his autobiography Cujo: The Untold Story of My Life On and Off the ice, he said that he regretted leaving Toronto. If he could have a do-over, you can bet your bottom dollar that he'd have stayed.
Following his departure from Toronto, Cujo made stops in Detroit, Phoenix and Calgary before signing back with the Maple Leafs in July 2008. In that season, he played backup to Vesa Tokala. Joseph played 21 games that year, including his 450th career win on December 30th, 2008, against the Atlanta Thrashers. In March 2009, the Leafs played against the Washington Capitals and Leafs goaltender Martin Gerber was ejected from the game. Joseph came in cold with 5 minutes left in the third period and put on a show, stonewalling the Caps and Alex Ovechkin, winning a shootout.
Cujo retired in January 2010 with 454 career wins in 943 games, putting him in fifth all-time. Even all these years later, Cujo is still 7th all time in that category. He also had 63 career playoff wins, the most by a goaltender to never win a Stanley Cup.
To this day, he is still loved by all Leafs fans, and is my personal all-time favourite Maple Leafs goalie.