Dexter hit three sixes against T&T but his new team lost by five wickets
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Middlesex may be forced to compete in December's Champions League without two of their recent acquisitions.
Neil Dexter and Neil Carter joined the club to play in the Stanford Twenty20 matches in the Caribbean and the Champions League in India.
But it has been suggested in India that only players registered with the county at the time of their Twenty20 Cup at the end of July would be eligible.
"There'll be frantic calls in the next 48 hours," skipper Shaun Udal said.
Carter joined Middlesex on a loan deal from Warwickshire and the move received clearance from the England and Wales Cricket Board.
But it was met with some scepticism, with England captain Kevin Pietersen openly critical.
Dexter, however, signed a two-year deal with the county shortly before the team left for the Caribbean.
They lost to England before going to down to a defeat to Trinidad & Tobago in a match said to be worth around £180,000.
Whether Dexter's connections with Kent, a team with links to the rebel Indian Cricket League, will cause further problems for Middlesex is uncertain.
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Hopefully we will get out to India and prove that we genuinely are a very good Twenty20 side
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It is thought the county have to disclose details of their squad to officials in India by the weekend.
"We don't know the playing conditions we are allowed to play under yet, so it is still up in the air," Udal added.
Indian franchises competing in the Champions League, which takes place from 3-10 December, are allowed to field up to four overseas players. But English county rules restrict the number Middlesex can use to one, who is spinner Murali Karthik.
"We are the sole representatives (from England)," Udal added. "We are going into the competition, albeit it appears not on the same playing field as other sides, with all the overseas players and people they can have.
"But at the end of the day we are there, representing our country and hopefully the pitches will suit us a bit more out there.
"There will be a bit more pace and carry and the pitches will turn a bit more.
"The pitch against Trinidad was very low and skiddy, so hopefully we will get out to India and prove that we are a genuinely very good Twenty20 side."
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