In the last six months Jurgen Klinsmann has coaxed the U.S. men's national soccer team to its first win over four-time World Cup champion Italy -- ending a 10-game losing streak that started in 1934 -- and an even more unlikely victory at Mexico, the first in 25 attempts on Mexican soil.

The only problem is that technically neither match mattered. Both were just friendlies.

That makes what comes next, a set of back-to-back 2014 World Cup qualifying matches against Jamaica, the biggest challenge of the U.S. coach's barely year-old tenure. Tied with a confident and MLS player-laden Jamaica at the top of its CONCACAF semifinal group, the U.S. needs at least one victory -- and perhaps more -- to ensure comfortable advancement into next year's final round of qualifying.

But Klinsmann won't have a full strength roster available Friday in Kingston -- where the United States is 0-0-4 in World Cup qualifiers -- or in the rematch four days later in Columbus, Ohio. Key midfielders Michael Bradley (quadriceps) and Landon Donovan (hamstring) are both injured.

That means Klinsmann must lean on Clint Dempsey, who hasn't played all summer while sorting out his recent transfer from Fulham. That Tottenham Hotspur would pay around $9 million for him -- Dempsey denied on Twitter that he will earn $22.2 million over three years -- shows just how important he is to the United States. But all the money in the world won't make up for lost match fitness, putting his 90-minute availability against Jamaica in doubt.

Klinsmann remains confident, and to be fair, Jamaica is 0-10-8 all time against the United States. But he has a pressing need for exactly what Dempsey offers as a withdrawn forward. Jose Torres struggled to generate offense against Mexico, while Brek Shea and Graham Zusi have never played in a qualifying match. Klinsmann also called in Norway-based Josh Gatt, only to see Gatt pull a hamstring, and D.C. United's Chris Pontius remains on the outside looking in.

Inevitably, attention will turn to Dempsey, who now shares something in common with his coach, playing where Klinsmann scored 20 goals during the 1994-95 Premier League season.

- Craig Stouffer