The team, which also consisted of frontenders Tim Belcourt and Kent Carstairs, first found success at the 1986 Blue Light Tankard, the provincial championship, where they had to win two playoff games before beating Wayne Tallon of Ottawa in the final.

In the playoffs, they beat British Columbia (Barry McPhee) in the semifinal before losing to Alberta's Ed Lukowich rink in the final.

The Howard rink won their second straight provincial title in 1987, defeating Ed Werenich in the final after beating Paul Savage in the semifinal.

The Howard rink had their best ever round robin showing up to that point at the 1988 provincial championships, finishing in first with a 7–2 record, giving them a bye into the final.

The team began the 1989–90 season with a new front end consisting of "a couple of former junior hotshots from Brampton" in cousins Wayne Middaugh and Peter Corner.

[16] The Howard four with Middaugh and Corner playing front end won their first provincial championship at the 1991 Blue Light Tankard, defeating London's Kirk Ziola in the final.

The team capitalized on a Ziola miss in the second, and then proceeded to hit everything in sight, to win the match 3–1, in an example of the low scoring defence oriented style in the pre free-guard zone era of curling.

The team won their second straight provincial Tankard in 1992, defeating future Olympic silver medallist Mike Harris and his Toronto Tam Heather rink in the final.

In the semifinal, the team downed Alberta's Kevin Martin rink, but they fell short in the final, losing to Vic Peters and Manitoba.

[19] A week later, the team played in the 1993 Seagram's VO Cup, the inaugural edition of the Players' Championship, the marquee event of the first World Curling Tour season.

Representing Canada the 1993 World Men's Curling Championship, the team led the round robin table with a 7–2 record, tied with Scotland's David Smith rink.

Following their win, there were rumours during the event that the team would decline the opportunity to represent Ontario at the 1994 Labatt Brier due to a dispute over not being allowed to use their sponsors on their sweaters.

In 1996, the Howards added 1994 Northern Ontario champions Scott Patterson and Phil Loevenmark to the team, replacing Corner and Herron.

At the 1997 provincial championship, the team did not fare as well as usual, finishing the round robin with a 5–4 record, tied with the Peter Steski rink from Ottawa City View.

[26] In 1997, the team again shuffled their front end, despite qualifying for the Olympic Trials, adding Herron back at second, and his junior teammate Steve Small from Toronto.

Earlier in the 2001–02 season, Team Howard won the TSN Skins Game, defeating Kevin Martin in the event's final, and taking home $77,200.

Team Glenn Howard was one of 18 rinks in the country to boycott the Brier in 2002 and 2003 due to a lack of prize money and inability to have sponsors.

A week later, the team played in the 2004 Ontario Men's Curling Championship, as the two-year boycott of many top curlers against the Brier had ended the previous fall.

However, they avenged this loss by beating the Americans 7–2 in the page playoff game and then winning the final over the Germans skipped by Andy Kapp, 8–3.

[43] Howard lost just one game en route to winning the 2009 provincial championship, including beating former teammate Peter Corner in the final.

While Martin was off at the Olympics, Howard swept through the 2010 Ontario Men's Curling Championship, going undefeated, including beating Bryan Cochrane in the final.

At the 2010 Tim Hortons Brier, Howard finished the round robin with an undefeated 11–0 record, but lost in the Final to Alberta's Kevin Koe.

In the playoffs, they beat Alberta (Kevin Martin) in the 3 vs. 4 game, then Newfoundland and Labrador (Brad Gushue) before losing to Manitoba (Jeff Stoughton) in the final.

[48] With Wayne Middaugh now throwing third stones on the team, the Howard rink won its fifth Masters at the 2011 World Cup of Curling, defeating John Epping in the final.

Howard won his 11th Grand Slam title at the 2012 Canadian Open of Curling, defeating future Olympic gold medallist Brad Jacobs in the final.

Team Howard would go on to lose to Manitoba's Jeff Stoughton in the page playoff and to eventual Brier champion, Northern Ontario's Brad Jacobs in the semi-final.

At the end of the 2013–2014 season, Glenn Howard announced that second Brent Laing would be leaving the team and going to Alberta to join with Kevin Koe's new rink.

[61] The team played with three players for much of the season, but brought back Adam Spencer to throw third stones, while Glenn's son Scott skipped at the Tankard.

The team reached the semi-finals at the expense of their Canadian counterparts; Howard said, "Too bad Canada were knocked out, but we've got a job to do and I'm really proud of the girls".

[75] Howard made a guest appearance on the CBC comedy Little Mosque on the Prairie on the season 2 episode titled "Jihad on Ice".