Sir Lucan is chasing back-to-back wins in the Winter Cup (2400m), but his second-up fitness is the key question this time around.

The gelding claimed last year’s edition at his fourth run from a spell. However, he’ll tackle Saturday’s Listed event with just one lead-up run — a last-place finish in the Lord Mayors Cup (2000m).

“He just got too far back the other day,” said co-trainer Adrian Bott.

“He can win a race of that quality at this time of year. But he is only second-up so he will probably improve again.”

Sir Lucan boasts two wins from four second-up runs and placed second in this year’s Gosford Cup after an unplaced return.

Only Destiny’s Kiss and Royal Bark have won the Winter Cup twice in nearly 70 years.

Stablemate Bear On The Loose also lines up, stepping up to 2400m for the first time.

“He is versatile in the conditions and should appreciate the trip,” Bott said.

Topweight Changingoftheguard resumes after a spring layoff.