1939)
Portsmouth's debut season in the First Division was a struggle. The next season they continued to falter, losing 10-0 to Leicester City, still a club record defeat. However, despite their failings in the league that season also saw Portsmouth reach the FA Cup final for the first time, which they lost to Bolton Wanderers.
Portsmouth managed to survive relegation, and their fortunes began to change. In the 1930-31 season the club finished 4th. The 1933-34 season saw Portsmouth again reach the FA Cup Final, beating Manchester United, Bolton Wanderers, Leicester City and Birmingham City on the way. Unfortunately the club was again defeated in the final, this time to Manchester City.
Having established themselves in the top flight, the 1938-39 season saw Portsmouth reach their third FA Cup Final. This time the club managed to defeat the favourites, Wolves, convincingly 4-1. Bert Barlow scored twice whilst Cliff Parker and Jock Anderson completed the famous victory.
League football was again suspended due to World War II, (however they did reach the 1942 London War Cup Final losing to Brentford at Wembley) meaning Pompey hold the unusual distinction of holding the FA Cup for the longest uninterrupted period, as the trophy wasn't contested again until the 1945-46 season. Nevertheless, with the Wartime Leagues in operation, Pompey signed various players of other clubs, who happened to be serving in the Forces and stationed near Portsmouth, on a temporary basis. One such was Andy Black of Glasgow Rangers, who on one notable occasion scored 8 goals in a 16 - 1 thrashing of Clapton Orient.
Read more about this topic: History Of Portsmouth F.C., Life At The Top (1927