Punters got the better of bookmaker Stan James last year with the chain showing a £285,800 loss against a profit of £2.8m in the previous year.
Turnover at the company, based in Newbury, Berkshire, dropped from £348m to £300.5m due in part to the economic downturn and increased competition, which led to the decision to sell its phone and online betting operations in February.
Stan James, founded in 1973 by entrepreneur Steve Fisher - it owes the name to Steve, his wife Anne and former partner James Holder - is owned by a parent company based in Gibraltar and was once among the biggest operators of phone and internet betting.
However, remote gambling operations were hit hard by a number of large payouts in the first half of 2008 as fewer than usual football matches ended in a draw, benefiting the punters, and popular horses such as Sea the Stars enjoyed winning streaks.
While turnover in its 19 shops was up due to the continuing popularity of fixed-odds betting terminals and the opening of new shops, margins fell, taking a toll on profits.