Having gone through two qualification rounds in booking a ticket for the 2002 World Cup along with the two-game home-and-home series against Grenada last summer and the six-game semifinal round that the Yanks survived this past fall Arena has seen just about everything.
There's no way that Arena expected his team to need a result down in Barbados just to move on the final round of qualifying back in 2000. Starting that final round with three straight wins - one coming against the vaunted Mexican side no less - and a 4-0-1 mark midway through the round was almost as surprising as the three-game losing streak that followed during that up-and-down run throughout 2001 to clinching a berth in South Korea.
Same goes with the late-game heroics that were seen in both Jamaica and Panama in 2004 that earned the U.S. critical points on the road only after many nervous moments when the side was down late in the second half of both matches.
That sort of caution is currently alive and well amongst the coaching staff and 23 players gathered here in Trinidad as the U.S. prepares for Wednesday's match (ESPN2 2:30 p.m. ET) against Trinidad & Tobago to start the final round of qualifying for the 2006 World Cup in Germany.
"Anywhere in the entire region makes for a difficult place to come and play said U.S. defender Greg Berhalter who has been through the rigors of qualifying the past two cycles. "Trinidad will be dangerous because their players have had all this time to think about this game and prepare for it. Plus with Carnival going on it's going to make the atmosphere that much more crazy."
The fact that Carnival is ending on Tuesday night will certainly spill over to Wednesday's match and make the Queen's Park Oval a virtual Lion's Den for the American side to walk into.
"They'll be very emotional said Arena of the Soca Warriors led by manager Bertille St Clair. "They'll have a huge home-field advantage playing in front of a capacity crowd playing on a field that probably won't be the best because the fact that it's a cricket ground and they've had events for Carnival there."
Having the match at the Oval is a bit of a gamesmanship move as the field is very low-cut for cricket and will play very fast which T & T hopes will help with the collective team speed they possess. Since various concerts have been held at the grounds over the past month it'll likely be a surface that has dirt patches and rough spots much like the field that the U.S. is used to playing on at The Office in Kingston Jamaica.
During the U.S. side's final training in Coral Gables Fla. on Monday morning before departing for Trinidad that evening Arena pitted what appeared to be the starting unit against a substitutes team in an 11 v. 11 scrimmage. If that is the case the "grey" team that could take the field on Wednesday afternoon had a back four of Cory Gibbs on the left Eddie Pope and Carlos Bocanegra in the central defense and Steve Cherundolo as the right back.
In the midfield Pablo Mastroeni lined up in a holding role behind Landon Donovan flanked by DaMarcus Beasley on the right and Eddie Lewis on the left. Up front the pair of Brian McBride and Eddie Johnson played together.
When changes were made midway through the scrimmage Josh Wolff went up top for McBride Ben Olsen and Clint Mathis took up spots in the midfield for Lewis and Mastroeni and Frankie Hejduk and Berhalter took out Cherundolo and Gibbs which pushed Bocanegra out to left back.
Donovan who trained with the side for two days in Miami after flying back from Germany where he now plays for Bayer Leverkusen looked particularly strong in both the scrimmage and in finishing exercises. Bocanegra stood out as well as did most of the European-based players in camp.
The only likely starter that wasn't on the field during Monday's scrimmage was goalkeeper Kasey Keller who arrived in Miami from Germany only 30 minutes before the team charter took off since he was in goal for Borussia Moenchengladbach on Sunday. Despite an all-day travel day that saw Keller fly from Duesseldorf to Frankfurt before heading to the U.S. Arena isn't worried about his veteran goalkeeper.
"It's been real difficult but Kasey has done this a lot said Arena who made Keller his No. 1 goalkeeper even before it became apparent that Brad Friedel was retiring from international play which he made official on Monday. "With a field player it'd be a lot more difficult. Kasey has been doing this for a lot of years and he understands how to deal with it."
The same goes for someone like Lewis who looked like one of the sharper players in training on Monday despite not getting to Miami until Sunday afternoon due to his Preston North End's match in England on Saturday.
"You are tired on the flight and you think about how you can get rest but then you land in the U.S. and you forget about it said Lewis. "You're so excited to be home - even for a day or two - and to be playing for your country that it doesn't matter. It really just takes a day to recover."
Trinidad & Tobago won't have nearly as many problems with jet lag or overtired players. The majority of the roster has been together for close to two months in Trinidad and has been playing tune-up matches for several weeks.
"They've had about six to eight games to prepare said Arena. "So I think they're going to be a handful."
Much like the U.S. T & T has a roster that includes several players who make a living overseas. The most notable player being Birmingham City striker Dwight Yorke who will be making his first appearance for his country in three-and-a-half years. While he is a far cry from the lethal scorer that he was with Manchester United in the '90s Arena said the Soca Warriors will be banking on his international experience.
In a 1-0 loss to Haiti on Sunday U.S. assistant coach Curt Onalfo said that Yorke played in a playmaker role behind the strikers and looked impressive. Since the days of the slick-passing Russell Latapy T & T hasn't had a true organizer in the midfield which makes Yorke's role even more vital in his return to the side.
Arena mentioned the tandem of Stern John (Coventry City) and Cornell Glen (FC Dallas) who are expected to play up top as the striker tandem in a 3-5-2 formation as well as standout goalkeeper Shaka Hislop as being key players to watch for the Soca Warriors. He also knows that his strikers will be tested by the size and power of the T& T defenders.
"They have physically dominating defenders in Marvin Andrews (Glasgow Rangers) and the like back there said Arena. "So they're pretty good there."
When looking at the opposing team U.S. assistant coach Mooch Myernick pointed out another player that could give the American some trouble in Southampton striker Kenwyne Jones.
"He's a big guy who they'll play out on the flank said Myernick. "Jones has played in the first and second divisions in England and now is in the Premiership so he has the type of experience that many of our overseas players have."
The U.S. players and coaches have said that the Trinidad & Tobago side is athletic and talented but many have also said to a man that it's not a side known for its consistency.
"They're so unpredictable said Berhalter. "Guys like Stern John and Dwight Yorke can change a game but you really just don't know what they'll bring on any particular day."
"It comes down to whether they can integrate their foreign-based players with their players who have been in camp said Myernick. "That's not always easy. Fortunately it's something our team is now used to and we have an incredible amount of experience in doing that. We know how to be a team. That's a strength that a lot of the other countries in the region can't match."
That's one of the reasons that this American side is expected to finish in the top half of the six-team group and earn a berth in its fifth straight World Cup come 2006. To do that it all starts down here in the West Indies where the U.S. hopes to send a message to the other teams around the region with a strong start out of the gate.
"Even in this past round of qualifying we learned that we have to have an attitude where we go away and get results said Donovan. "We are not playing to get ties on the road but we're going (on the road) to win games."
Marc Connolly covers soccer for ESPN.com. He can be reached at email@example.com.