Income tax

Lipson v. Canada, 2009 SCC 1
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(Tax / Income Tax / GAAR)
L and his wife bought a family residence, then entered a series of transactions involving a mortgage and a loan to buy shares in a family corporation.  Mortgage funds were used to repay the share loan, and L deducted mortgage interest payments and reported share taxable dividends over the following years.  The Minister of National Revenue disallowed the deductions.  The Court held that under the general anti-avoidance rule ("GAAR"), the deductions should be disallowed.
Majority/Dissent/Dissent: 4/2/1

R. v. McLarty, 2008 SCC 26
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(Taxation / Income tax)
In 1992, M bought an interest in proprietary seismic data, with payment satisfied by a down payment and a promissory note, repayable according to a somewhat complex scheme.  M treated his purchase as a largely deductible expense, but was reassessed.  The Court found that M was entitled to his deduction, since he incurred an absolute liability.  M and the seller dealt with each other at arm's length.
Majority/Dissent: 7/2