On January 14, 2008 at Santa Anita, Wait A While contested the Grade II San Gorgonio Handicap a race which had been postponed for a week as the racecourse struggled with drainage problems caused by the newly installed Cushion Track. Starting the odds-on favorite against four opponents, she raced in third place before taking the lead a quarter of a mile from the finish and winning by one and a half lengths from Lavender Sky. Commenting on the mare's relatively unimpressive performance, Gomez said "She was looking around, and I couldn’t get her focused on her task [but] when I found a spot, she did what she was supposed to do". Wait A While then sustained a stress fracture to her left tibia and was off the course for more than six months. Wait A While returned for the Grade I Diana Stakes at Saratoga on 26 July. Ridden for the first and only time by Rafael Bejarano she was made the 3.05/1 favorite but finished seventh of the ten runners almost six lengths behind the winner Forever Together. On August 21, the mare attempted to repeat her 2007 success in the Ballston Spa Handicap and started the 0.85/1 favorite against four opponents. With John Velazquez reclaiming the ride, Wait A While tracked the leader Sharp Susan before taking the lead entering the stretch and held off the challenge of Carriage Trail to win by a length. Pletcher expressed the view that the firmer ground had been the key to the mare's improved performance and added "She’s a special filly... she’s won some tremendous races. This is her fourth year at Saratoga, so when you have one that long, it gets a little extra special". On 27 September, Wait A While attempted to become the first horse to win the Yellow Ribbon Stakes for a second time. Ridden by Velaquez she started favorite ahead of the New Zealand-bred Black Mamba (winner of the John C. Mabee Handicap) and Vacare. After racing in third place on the outside, the mare took the lead entering the stretch, accelerated into a clear lead, and held off a challenge from Vacare to win by three-quarters of a length, with Black Mamba a length away in third. Velazquez reported that the mare "got a little bit aggressive with me when we started down the backside, but she does everything easy and I was able to bide my time.