Five years later, at the 1996 Labatt Brier, Stoughton and his team of Tresoor, VanDenBerghe, and Steve Gould went all the way, losing only two games en route to the championship, defeating Kevin Martin of Alberta in the final.

Stoughton would return to the 1999 Labatt Brier with 2 new players, Jon Mead and Doug Armstrong replacing Tresoor and Gould.

He finished the round robin in 2nd place behind the Brad Gushue rink (skipped for this event by Russ Howard throwing second stones), and defeated then John Morris in the semifinal.

In the final, Gushue made a steal of two in the 4th end which put Stoughton in a 6-2 hole, which proved to be costly.

Stoughton would win the 2007 Manitoba Championship with a new lineup of Ryan Fry, Rob Fowler, and Gould, defeating Peter Nicholls in the final.

[5] The move proved to be fairly successful, as Stoughton led his new team to the final of the 2009 Tim Hortons Brier in which they lost to Kevin Martin.

[7] Jeff brought back his past longtime third Jon Mead, while also acquiring Reid Carruthers to play at second.

With a new team of Jon Mead and Reid Carruthers, Stoughton won the 2011 Safeway Championship in Manitoba to qualify for the 2011 Tim Hortons Brier.

There in London, Ontario, the team finished second in the round robin and went on to defeat Glenn Howard in the final 8-6, capturing Stoughton's third Brier championship.

Stoughton failed to reach the 2012 Tim Hortons Brier after losing to eventual provincial champion Rob Fowler in the quarterfinals of the 2012 Safeway Championship.

Following his retirement in 2015 as a professional curler, Stoughton served as a coach for Team Canada's mixed doubles at the 2018 Winter Olympics in Pyeongchang, Korea.

[12] He would serve as coach for Kaitlyn Lawes and John Morris as they won the Olympic gold medal.

[12] He currently serves as Curling Canada's men's and mixed doubles national coach and program manager.