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The 2008 season began with a 6 – 0 record with wins shared between three quarterbacks, including the season opening starter, Marcus Crandell.
This was the team's best record since 1934 when they were still known as the Regina Roughriders.
On August 24, 2008, the team's General Manager, Eric Tillman, announced the acquisition of Quarterback Michael Bishop, the Toronto Argonauts backup quarterback at the time of the trade, who went 11 – 1 as a starter for the Argonauts in 2007.
This was the end of Marcus Crandell's run with the Roughriders, as he was released four days later.
After the 6 – 0 start, the Riders would go on to finish the 2008 CFL Regular season with the same record they finished with in 2007, at 12 – 6.
The Roughriders finished in second place in the CFL West Division and earned the right to host the CFL West Division Semi-Final for the second consecutive year.
The Roughriders suffered a devastating 33 – 12 loss to the BC Lions in the western semi-final game, leading to Bishop's release shortly after the loss.

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