Five has so far received bookings from Expedia, Sony Ericsson, Tesco and the Central Office of Information to run interactive ads on Sky Digital using its iTV technology.
ITV launched its first interactive campaign through iTV in January this year, with Channel 4 close behind.
Five is aiming to receive around 100 bookings in the first year, drawing potentially seven-figure revenue.
Damon Letzer, interactive business controller at Five, said: "We will be working closely with our agencies and with other broadcasters to raise awareness of interactive advertising. This is an opportunity for bringing more money into the TV market."
At present, the interactive ads will only be accessible to viewers in 7m Sky Digital homes accounting for 20% of Five's audience base.
The trend for interactive advertising is expected to grow, with broadcasters in production with ZipTV about using it as a provider of interactive services as well as iTV.
Will Harding, commercial director for partnerships at Sky Interactive, said: "The ability to run campaigns across multiple channels is the key to growth of iTV, so Five's entry is an important step forward for this exciting new medium."
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