Rickler progressed through the youth academies of Pistoiese, Pisa and Chievo before making his senior debut. He made his first-team debut on 18 April 2007, appearing for Chievo in Serie A away at Lazio in a 0–0 draw. His time with the Chievo first team amounted to four Serie A appearances and seventeen in Serie B, with much of his career at the club spent on loan to Serie B sides including Piacenza and Modena.
In June 2011 Rickler was exchanged with Alessandro Bassoli in a co-ownership deal, both players' 50 per cent registration rights tagged at €1.5 million each, and he signed a five-year contract with Bologna. The deal attracted criticism as an exercise in creative accounting: the inflated valuations boosted the clubs' 2010–11 financial results through the reporting of selling profit while creating ongoing amortisation costs of approximately €600,000 per season for five years.
Rickler was questioned by prosecutors from March 2012 in relation to the 2011–12 Italian football scandal. On 18 June 2012 he was suspended for four years. His Piacenza and Chievo teammate Alessandro Sbaffo negotiated a plea bargain that reduced his own ban to three years and three months in exchange for a heavy fine; Rickler retained legal representation and contested the charge but failed to secure an acquittal. An appeal to the Corte di Giustizia Federale was dismissed on 6 July 2012. A further appeal to the Tribunale Nazionale di Arbitrato per lo Sport resulted in the suspension being shortened to fourteen months.
Bologna, facing a residual contract value of approximately €2.4 million that would never be recovered under the original four-year ban, wrote down Rickler's contract value during the relevant financial year. Following the ban's reduction the write-down was reversed. Both clubs gave up their bought-back rights in June 2012. With his ban shortened further in April 2013, Rickler joined fourth-division Mantova on 21 August 2013, and moved on loan to Prato in July 2014. He retired from football in 2015.
After leaving professional football, Rickler turned to motorsport, competing in rally raid events in the trucks category. His Dakar Rally record:
| Year | Class | Vehicle | Result | |------|-------|---------|--------| | 2017 | Trucks | Iveco | 40th | | 2019 | Trucks | — | Not classified | | 2020 | Trucks | — | Not classified | | 2022 | Trucks | MAN TGS (R Team, co-driver Dragos Razvan Buran) | DNF | | 2023 | Trucks | MAN (R Team, co-driver Oscar Bravo Garcia) | DNF | | 2024 | Trucks | MAN TGS (TH-Trucks Team, with Aldo and Dario de Lorenzo) | 46th | | 2025 | Trucks | MAN TGS (TH-Trucks Team, co-driver Aldo de Lorenzo) | Retired Stage 12 |
His 2024 finish of 46th overall represented his best classified result in the event. His involvement in the Dakar Rally highlights a complete career pivot from team sport to one of motorsport's most demanding endurance disciplines.