The exercise was carried out in Todmorden, Hebden Bridge, Mytholmroyd, Sowerby Bridge, Elland and Brighouse.
About 2,700 homes were flooded along with more than 4,400 businesses in the area in 2015, said Calderdale Council.
Scenarios played for the exercise included a mock rescue of casualties from a sinking canal boat.
Operation Calderdale16 was its biggest ever live training exercise, the council said.
The Environment Agency has eight flood sirens to warn the upper Calder valley when rivers are expected to flood.
The sirens sounded for about two minutes during the exercise.
Source: Eye on Calderdale

The France midfielder has accepted a violent conduct charge for the incident during Saturday's goalless draw.
Sissoko, 27, apologised but was charged by the Football Association. Spurs will not appeal against the decision.
His suspension will include Tuesday's EFL Cup tie at Liverpool, plus league games against Leicester and Arsenal.
The FA said the incident was missed by match officials.
"I need to say the elbow was in the face of Arter and it is clear," Spurs manager Mauricio Pochettino said on Monday.
"We are in a period where we need all the squad, all the players to compete. It's difficult now because he is a player who was in our plans to play tomorrow, so we have to change a little bit."
Speaking to Match of the Day after Saturday's game, Arter said he was happy to accept Sissoko's explanation that the contact was accidental.
He said: "I never want to see a player get into trouble if they didn't mean to. Sissoko apologised. I'm happy to move on from it."
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The bird and wildlife charity was due to unveil its new sites at Snape and Hollesley later.
However, the flooded River Alde over-topped the reserve at Snape, filling the freshwater marshes with saltwater.
Work to clear up the damage is continuing and the RSPB said it hoped to open the reserves in the spring.
Aaron Howe, RSPB reserves project manager, said: "The rain has helped flush out virtually all of the salt and the marsh will recover, but the project has been delayed."
The 125-acre marsh at Snape is an extension to the existing 70-acre reserve.
The reserve at Hollesley was not flooded, but the RSPB was hoping to formally open it on the same day as it opened Snape.
Flood sirens have sounded as the "biggest ever" training exercise has been held in parts of West Yorkshire inundated by flooding in December 2015.
[NEXT_CONCEPT]
Tottenham's Moussa Sissoko will be banned for three matches for elbowing Bournemouth's Harry Arter, missing the north London derby with Arsenal.
[NEXT_CONCEPT]
The RSPB has had to cancel the opening of its two new reserves in Suffolk due to damage created by December's coastal surge tides.