The Ranji Trophy, 1938-39 started on 28th October, 1938 with the match between Baroda and Bombay in Baroda. There were a number of 18 teams that participated in the fifth edition of the tournament and the teams included Baroda, Bengal, Bihar, Bombay, Central India, Delhi & Districts, Gujarat, Hyderabad, Madras, Maharashtra, Mysore, Northern India, Nawanagar, North West Frontier Province, Rajputana, Sind, United Province and the Western India. The first match was held at Baroda from 28-30 October, 1938 and the Bombay was declared as the winner in the drawn match for having a lead in the first innings of he match. The second match involved the teams of Western India and Maharashtra and the match was held at Rajkot from 04-06 November, 1938. The Western India team won the match by 110 runs.

The third match of the tournament saw the clash between the teams of Nawanagar and Gujarat at Jamnagar from 04-06 November, 1938. The Nawanagar team won the match by 8 wickets and the next match saw the teams of Sind and Bombay competing with each other at Karachi. The match was held from 05-07 November, 1938 and the match was drawn. The fifth match was held at Jamnagar from 09-11 November, 1938, between the teams of Nawanagar and Western India. The teams of Rajputana and Southern Punjab met in the sixth match of the Ranji Trophy, 1938-39, held at Patiala from 12-14 November, 1938 and the Southern Punjab team won the match by 184 runs. In the seventh match of the tournament, the teams of Hyderabad and Mysore clashed with each other at Secunderabad from 25-27 November, 1938 and the drawn match was won by the Hyderabad team, for having a lead in the first innings.

The next match saw the North-West Frontier Province and the Delhi & Districts team playing against each other at Peshawar from 26-28 November, 1938. The North-West Frontier Province team won the match by a big margin of an innings and 171 runs. The Bengal and Bihar team clashed with each other in the ninth match of the Ranji Trophy, 1938-39 at Calcutta from 03-04 December, 1938. The Bengal team won the match comprehensively by an innings and 185 runs. The next match, held at Indore from 10-12December, 1938 and it involved the teams like Central India and United Provinces. The winner of the match was Central India, which won by 246 runs. In the eleventh match of the tournament, the teams like Madras and Hyderabad locked their horns together at Madras from 17-19 December, 1938 and Madras won the battle by 6 wickets. The next match was held at Karachi from 24-26 December, 1938 between the Sind and Nawanagar team and it saw the Sind team winning the drawn match, due to its lead in the first innings.

In the thirteenth match of the tournament, the teams like Bengal and Central India faced each other at Calcutta from 31 December, 1938 - 02 January, 1939 and the Bengal team successfully beat their opponents by an innings and 121 runs. The Southern Punjab and North-West Frontier Province then met with each other at Patiala from 02-04 January, 1939 for the fourteenth match of the Ranji Trophy, 1938-39. The Southern Punjab team won the match quite convincingly by an innings and 37 runs. In the match between Northern India and Army, the Northern India team was declared the winner, even without a ball was bowled, as the Army team could not appear on the field.

The last match of the group level was held between the teams of Southern Punjab and Northern India at Patiala from 21-23 January, 1939. The Southern Punjab team won the match by 9 wickets and proceeded towards the Semi-Finals of the tournament. The first Semi-Final match of the Ranji Trophy, 1938-39 involved the teams like Bengal and Madras and it took place at Calcutta from 21-24 January, 1939. Bengal entered into the Final of the tournament by winning the match by an innings and 285 runs. The second Semi-Final match saw the teams of Southern Punjab and Sind locking their horns together at Patiala from 10-12 February, 1939. It saw the Southern Punjab team winning the match by 7 wickets ton set a Final clash with the Bengal team. The Final match was held between Southern Punjab and Bengal at Calcutta from 18-21 February, 1939 and Bengal became successful to win the Ranji Trophy for the first time, after beating the Southern Punjab team by 178 runs.