In the autumn of 2014, he was moved up in class and won the Phoenix Stakes at Keeneland and followed up with an upset win over a strong field in the Breeders' Cup Sprint.
Work All Week was a chestnut gelding with a white blaze bred in Illinois by Richard and Karen Papiese's Midwest Thoroughbreds Inc. His sire City Zip, a half-brother to Ghostzapper, showed his best form as a two-year-old in 2000 when he won the Hopeful Stakes and dead-heated for first place in the Belmont Futurity.
Over the same course and distance in June, he started 1/5 favourite for the Addison Cammack Handicap (restricted to horses bred in Illinois),[6] but sustained his only defeat of the year when he was caught in the final strides and beaten a nose by the gelding Sweet Luca.
On his final appearance of the year, he faced Sweet Luca and Signsealdeliver in the Lightning Jet Handicap at Hawthorne in November and was made the 3/5 favourite.
After a break of over three months, the gelding reappeared in the Iowa Sprint Handicap at Prairie Meadows on June 28 on a muddy track against five opponents.
Ridden as in the Hot Springs Stakes by Christopher Emigh he went to the front from the start and then rallied after being overtaken in the straight to regain the lead and win by half a length from the favoured Delaunay.
[11] A month later Work All Week made his second attempt to win the Addison Cammack Handicap and started 7/10 favourite under top weight of 130 pounds.
[12] On his fourteenth track appearance, in the autumn of his five-year-old season, Work All Week was moved up to Grade III class for the first time when he contested the Stoll Keenon Ogden Phoenix Stakes over six furlongs at Keeneland Racecourse.
Florent Geroux, who had partnered the horse in some of his early races, took over the ride from Emigh and Work All Week started the 11/5 favourite against six opponents.
He started a 20/1 outsider against opponents including the Hong Kong-trained Rich Tapestry (winner of the Santa Anita Sprint Championship on his American debut), Secret Circle (winner of the race in 2013), Private Zone (Vosburgh Stakes), Palace (Forego Stakes) and Big Macher (Bing Crosby Handicap).