[4] Redden played minor hockey with the teams at Hillmond High School, and the Mid West Red Wings, which were from the rural area.

After that, he played one year with the Lloydminster Blazers, before joining the Western Hockey League (WHL)'s Brandon Wheat Kings for the 1993–94 season.

Redden was originally selected second overall by the New York Islanders in the 1995 NHL Entry Draft, but never played for the team – he was traded in a three-team deal with the Ottawa Senators and Toronto Maple Leafs that saw his rights, along with Kirk Muller, Ken Belanger, Damian Rhodes, Don Beaupre, Martin Straka and the rights to Bryan Berard move between the teams on January 23, 1996.

[5] Redden would be named NHL Rookie of the Month for April 1997, and was an important part of the team's drive to qualify for the Stanley Cup playoffs that season;[6] The appearance was the first in modern Senators' history.

[7] Near the end of the season, however, he suffered an ankle injury, forcing him to miss the 2000 playoffs, a contributing factor in the Senators losing in the first round to the Toronto Maple Leafs.

The Senators ultimately chose to retain Redden, and the two agreed on a two-year, $13 million contract with a no-trade clause; Chára signed instead with the Boston Bruins.

Newly promoted general manager Bryan Murray attempted to trade Redden to the Edmonton Oilers during the 2007 NHL Entry Draft.

Trade rumours would swirl around Redden for most of the season, though he remained a starter with the team and played in his 800th career NHL game on January 10, 2008, against the Buffalo Sabres.

In February 2008, it was revealed that Redden used the no-trade clause in his contract to kill a deal that would have sent him to the San Jose Sharks in exchange for Matt Carle and a draft pick.

Within weeks of the aborted trade, the Sharks surpassed Ottawa in the League-wide standings, and the Senators performance continued to decline; the coach was eventually fired and the team struggled into the playoffs.

[16] Speaking in 2013 on his stint with the Rangers, Redden said, "I think maybe making that money there and being the player I am… I felt like the first little while, things were going pretty good, and then they kind of fell off.

However, the buyouts cannot be used on injured players, so, to avoid any risk of a hockey-related injury, the Rangers originally instructed Redden to simply not report to camp.

While this meant that Redden (along with Scott Gomez of the Montreal Canadiens, who was in a similar situation) would still have been paid his prorated 2012–13 salary despite not playing, the NHL Players' Association (NHLPA) was concerned that for Redden and Gomez to be forced to spend an entire year away from hockey would adversely affect their ability to find employment elsewhere in the NHL during the 2013 off-season, even at a much reduced salary.

[25] He scored his first goal back against the Dallas Stars on January 26, and played his 1,000th career NHL game on February 7, against the Detroit Red Wings.

In the first game of the conference quarterfinals series of the 2013 Stanley Cup playoffs, Redden scored a goal and added an assist in the Bruins' 4–1 victory over the Toronto Maple Leafs.

[29] On June 27, 2016, Redden joined the Nashville Predators organization as assistant director of player development,[30] specifically to evaluate prospects and ease their transition to the NHL with mentorship.

[32] Redden sponsored a suite at Scotiabank Place, named Wade's World and reserved for critically and terminally ill children, while a member of the Senators from 1997 until 2008.

In 2015, Redden was honoured by the Brandon Wheat Kings as he was awarded for alumni achievement and was recognized as one of the WHL's top 125 players of all time.