The Canadian duo of Dwayne De Rosario and Frank Yallop collaborated to bring two MLS Cups to San Jose in 2001 and 2003.
But the pair could not replicate their success in CONCACAF qualifying for the 2006 World Cup. Yallop left San Jose after the second Cup triumph to take charge of the Canadian national side, but they fell in the semifinal round after drawing a difficult group featuring Costa Rica, Honduras and Guatemala.
With the Canadian World Cup dream pushed off until 2010, Yallop has been able to experiment with younger talent during the CONCACAF Gold Cup with an eye towards the next round of qualification.
The young talent showed well during the Gold Cup, although Tuesday night's 2-1 victory against Cuba was not enough to gain a quarterfinal berth after losses to group winners USA and second-placed Costa Rica.
"If you look at all of our games, we struggled to score goals," said Yallop. "I was frustrated with our finishing. All in all, there were chances we should have taken."
"This is not as good as I wanted," said De Rosario. "This is not what we planned. However, we have a new team and we created lots of chances."
Yallop's experiments have seen the versatile De Rosario line up on the left flank. A striker by trade, De Rosario has featured as an attacking midfielder for the Earthquakes for most of this campaign after the departure of Landon Donovan in the close season.
"I think Frank is just trying to get as many attacking players out on to the field as possible," said De Rosario. "I play attacking midfield in San Jose, and I'm just trying to get lots of through balls to the forwards."
Younger players, such as the strike duo of Ali Gerba and former MetroStars draftee Olivier Occean, form the core of the 2010 effort.
"We're trying to work with the young guys," said Yallop.
De Rosario is looking forward to the next round of qualification with a keen eye, as he feels that he can continue with the side through the next cycle.
"I am fit enough," said De Rosario. "I'll do my best to help us qualify for 2010. If we keep playing like we did in this tournament and score some goals, I think we will qualify."
With Canada's 2005 Gold Cup experience now concluded, Yallop can look towards the future with a younger generation of Canadians in the hopes of developing a World Cup-caliber squad for 2010.
"We have to take the positives," said Yallop. "I think the worst game we played [in the tournament] was [against Cuba]. We created lots of good chances, but we didn't really put it all together. Finishing chances was the one thing we were missing."
Kyle McCarthy is a contirbutor to MLSnet.com. This story was not subject to the approval of Major League Soccer or its clubs.