Born in Johannesburg, Gauteng, Dolly started playing football at Westbury Arsenal, then later he moved to School of Excellence where he was spotted by Mamelodi Sundowns.

Sundowns were eliminated by AS Vita Club in the third round of the Caf Champions league but with the turn of events AS Vita Club were eliminated in the competition due to the finding that they had used an ineligible player during the preliminary matches of the 2016 Orange CAF Champions League.

[8] On 25 June 2024, public broadcaster SABC reported that Dolly, along with teammates Sifiso Hlanti and Siyethemba Sithebe, would be leaving the club upon the expiration of his contract at the end of the month.

[11] Dolly played for the under 23's and represented his country during the 2015 Africa U-23 Cup of Nations tournament which was held in Senegal.

Dolly captained the South African side during the 2016 Summer Olympics men's football tournament.

His extreme pace and close control allows him to roam into pockets of space around the pitch in the same way as Manchester United playmaker Juan Mata.