He was a four-sport star (football, basketball, soccer, and track) at Oakville's White Oaks High School, and originally enrolled at Michigan State as a quarterback in 1988. However, he left Michigan State for a California junior college, where he punted and played quarterback. He returned to major-college football as a punter and placekicker at West Virginia University, starring in both roles in 1991 and 1992.

After graduating from WVU in 1993, he returned to Canada and started a career in the CFL. He played briefly for the Saskatchewan Roughriders in 1993. He did not play in 1994 or 1995. Vanderjagt returned to the league in 1996 with the Toronto Argonauts, serving as the regular placekicker and punter. He led the CFL in yardage per punt in 1997, and the Argos won the Grey Cup in both 1996 and 1997.

In 1996, Vanderjagt also played for the Minnesota Fighting Pike of the Arena Football League.

In 1998, Vanderjagt crossed the border and joined the Indianapolis Colts, and was a fixture as the club's placekicker until the end of the 2006 season. He led the NFL in scoring in 1999, and is now the most accurate field-goal kicker in the league's history (217-248, 87.5 t the end of the 2005 season).

After the 2002 season, Vanderjagt put himself in the center of a media firestorm in an interview for the Canadian cable sports network The Score. He said that Colts quarterback Peyton Manning needed to show more emotion, and implied that head coach Tony Dungy was too placid and not enough of a motivator. He apologized several days later for his remarks, but Manning later fired back in a sideline interview at the Pro Bowl, referring to him as "our idiot kicker who got liquored up and ran his mouth off."

Vanderjagt had a spectacular 2003 season, becoming the first kicker in the league's history to go an entire season, including the playoffs, without missing a field goal or point-after attempt. (In 1998, Gary Anderson was perfect in the regular season, but missed a key field goal attempt in the playoffs.) In the process, he made his first Pro Bowl. He finished the regular season 37 for 37 in field goals and 46 for 46 in PATs. He was also perfect on three field-goal attempts and 12 PATs in the postseason. Vanderjagt's streak of 42 consecutive successful field goal attempts, the longest in NFL history (the league does not include postseason games when compiling streaks), ended on September 9, 2004 when he missed a 48-yard attempt against the New England Patriots.

In 2004, he kicked 20 field goals, the lowest number of his career. However, he also had considerably fewer field goal chances that season (25), as the Colts offense scored 61 touchdowns (nearly four per game), with Manning throwing an NFL-record 49 TD passes.

After the Colts routed the Denver Broncos in the wild-card round of the 2004 playoffs, he told reporters that the Colts' opponents in the next round of the playoffs, the New England Patriots, were "ripe for the picking," and also said "I think they're not as good as the beginning of the year and not as good as last year" (when they won the Super Bowl). Patriots safety Rodney Harrison fired back at him in an interview, calling him "Vanderjerk". Harrison's teammate, linebacker Willie McGinest, was more temperate in his response, but noted that "there's going to be a whole bunch of plays when he's not going to be out there . The rest of his guys will be out there dealing with it." The Patriots eventually defeated the Colts 20-3 and went on to win the Super Bowl.

Vanderjagt indicated in a radio interview during the season that he may not return to the Colts for 2005, as his cap number is $2.8 million and the Colts may not be willing to pick up his salary for that season. He noted that he may return to the CFL, where his professional career began. However, he eventually signed a reworked deal and returned to the Colts.

In the 2005 NFL Playoffs, in a tightly contested game against the Pittsburgh Steelers, Vanderjagt kicked a 46-yard field goal attempt wide right with 18 seconds remaining, when the Colts were behind 21-18, costing the Colts a chance at overtime and ending the team's season. Walking off the field after the kick, he took off his helmet and smashed it in the ground in disgust which cost his team a meaningless 15 yard personal foul (unsportsmanlike conduct) penalty.

Shortly thereafter, on January 19th, 2006, Vanderjagt appeared on a lighthearted segment of the Late Show with David Letterman, during which he successfully kicked a 46-yard field goal, outsite Letterman's Manhattan studio. The famed host served as his holder.

Discussing his catastrophic miss with Letterman, Vanderjagt joked that, "All the Steeler fans on the left side of the stadium, they all blew at the same time," and defended quarterback Manning against criticism, calling him the "Tiger Woods and Michael Jordan of football."

In the 2006 offseason, the Colts released Vanderjagt to make room to sign free agent Adam Vinatieri, the kicker who had played an important part in the Patriots' recent successes. On March 23, he signed a three-year deal with the Cowboys.