The 1994 – 1995 season proved to be a debacle for Plymouth Argyle as they were very disappointing in the second division, finishing the campaign off in a dismal 21st position, in turn demoting the club in to the fourth tier of English football for the first time in the football clubs history. They also crashed out of the League cup in the first round, suffering a 5-2 aggregate defeat against Walsall in the cup competition.
The 1995 – 1996 season saw Plymouth emerge in to a dominant force in the third division as they gained promotion via the play offs as they finished the campaign off in an impressive fourth position. Chris Billy and Paul Wotton enjoyed an outstanding season for the club through out. The Pilgrims found life difficult to adapt to in the second division, however survive at the end of the 1996 – 1997 season with a 19th position finish.
The 1997 – 1998 season proved to be a disaster for the club as they crashed out of the FA cup and league cup in the first round as they suffered defeats against Oxford United and Cambridge United in the first round. They also finished of the campaign in 22nd position, in turn relegating the club back in to the third division.