News Releases

/NOT FOR DISTRIBUTION TO UNITED STATES NEWSWIRE SERVICES OR FOR
    DISSEMINATION IN THE UNITED STATES/

    TSX SYMBOL: TDGCALGARY, June 4 /CNW/ - Trinidad Drilling Ltd. ("Trinidad" or the
"Corporation") is pleased to announce it has entered into an agreement with a
syndicate of underwriters led by Raymond James Ltd. (Raymond James) and
including TD Securities Inc., RBC Capital Markets, Scotia Capital Inc., CIBC
World Markets Inc., Haywood Securities Inc., Canaccord Capital Corporation,
FirstEnergy Capital Corp. and Wellington West Capital Markets Inc.
(collectively the "Underwriters"), to offer on a bought deal basis, by way of
a short form prospectus, 27,184,500 common shares at a price of $5.15 per
share for gross proceeds of approximately $140 million (the "Offering"). In
addition, the Underwriters have been granted an over-allotment option to
purchase an additional 1,941,750 common shares under the same terms, which
over-allotment option is exercisable for a period of 30 days following the
closing of the Offering. If the over-allotment option is exercised in full,
the gross proceeds of the Offering to Trinidad will be approximately $150
million. The net proceeds of the Offering will be used to reduce the
Corporation's indebtedness. The increased financial flexibility resulting from
this debt reduction will provide Trinidad with the ability to evaluate, and if
appropriate, capitalize on value-creating opportunities in potential new and
existing markets.
    Participants in the current financing will receive the second quarter
dividend provided they are a shareholder of record on the record date.
Trinidad's Board of Directors has declared its second quarter dividend to be
$0.05 per share payable on July 15, 2009 to shareholders of record on June 30,
2009. This dividend is designated as an "eligible dividend" for Canadian
Income Tax purposes.
    Closing of the Offering is anticipated to occur on or about June 25,
2009, and is conditional upon the receipt of all necessary regulatory
approvals.
    While the availability of common shares under the Offering is subject to
overall demand and cannot be assured, Trinidad has requested that Raymond
James take reasonable steps to attempt to facilitate participation in the
Offering by existing Trinidad shareholders. Existing Canadian shareholders
should contact their Raymond James representative, or their individual
investment advisor, as soon as possible for more information.
    Trinidad is a growth-oriented corporation that trades on the Toronto
Stock Exchange (TSX) under the symbol TDG and TDG.DB. Trinidad's divisions
operate in the drilling, well-servicing, coring and barge-drilling sectors of
the North American oil and natural gas industry. With the completion of the
2009 rig construction program, Trinidad will have 119 land drilling rigs
ranging in depths from 1,000 - 6,500 metres and operations in Canada, the
United States and Mexico. In addition to its land drilling rigs, Trinidad has
23 service rigs, 20 pre-set and coring rigs and 4 barge rigs currently
operating in the Gulf of Mexico. Trinidad is focused on providing modern,
reliable, expertly designed equipment operated by well-trained and experienced
personnel. Trinidad's drilling fleet is one of the most adaptable,
technologically advanced and competitive in the industry.

    Advisory Respecting Forward-Looking Statements

    This news release contains certain forward-looking information and
statements within the meaning of applicable securities laws. The use of any of
the words "expect", "anticipate", "continue", "estimate", "objective",
"ongoing", "may", "will", "project", "should", "believe", "plans", "intends",
"confident", "might" and similar expressions are intended to identify
forward-looking information or statements. In particular, but without limiting
the foregoing, this news release contains forward-looking information and
statements that involve substantial known and unknown risks and uncertainties,
certain of which are beyond Trinidad's control, including the following: (i)
the completion of the rig construction programs on a timely basis and on
economical terms; (ii) the ability of the Corporation to complete the
Offering, including receiving the necessary regulatory approvals therefor;
(iii) the assumption that Trinidad's customers will honour their take-or-pay
contracts; (iv) the ability for Trinidad to attract and retain qualified crews
to crew their rigs; (v) assumptions respecting capital expenditure programs
and other expenditures by oil and gas exploration and production companies;
(vi) assumptions respecting commodity prices, foreign currency exchange rates
and interest rates; (vii) assumptions respecting supply and demand for
commodities; and (viii) other expectations, beliefs, plans, goals, objectives,
assumptions, information and statements about possible future events,
conditions, results of operations or performance. Various assumptions were
used in drawing the conclusions or making the projections contained in the
forward-looking statements throughout this news release.
    The forward-looking information and statements included in this news
release are not guarantees of future performance and should not be unduly
relied upon. Forward-looking statements are based on current expectations,
estimates and projections that involve a number of risks and uncertainties,
which could cause actual results to differ materially from those anticipated
and described in the forward-looking statements. Such information and
statements involve known and unknown risks, uncertainties and other factors
that may cause actual results or events to differ materially from those
anticipated in such forward-looking information or statements.
    Trinidad cautions that the foregoing list of assumptions, risks and
uncertainties is not exhaustive. The forward-looking information and
statements contained in this news release speak only as of the date of this
news release, and Trinidad assumes no obligation to publicly update or revise
them to reflect new events or circumstances, except as may be required
pursuant to applicable securities laws.

    This news release shall not constitute an offer to sell or the
solicitation of an offer to buy the shares in any jurisdiction. The shares
offered will not be and have not been registered under the United States
Securities Act of 1933 and may not be offered or sold in the United States or
to a United States person, absent registration, or an applicable exemption
therefrom.