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Contracts
Crosslinx Transit Solutions (CTS), a consortium of more than 26 companies, was awarded the contract to design, build and finance the central section, and maintain it for 30 years. The contract excludes boring the tunnels, and covers all other remaining work, including the stations and the finishing work within the tunnels. CTS consortium members include SNC-Lavalin, Aecon, EllisDon, ACS Infrastructure Canada, Dragados, IBI Group and Scotiabank. The contract defines a public–private partnership. The 30-year contract to build and maintain the line will total $9.1billion. Capital costs will be $5.3billion, with each of the 15 underground stations costing $80–$100million to build and the ten street-level stops $3–$5million each. The remainder will be for financing, lifecycle and maintenance costs.

In July 2015, Crosslinx awarded Bombardier Transportation a 30-year contract to maintain Line 5's light-rail vehicles. The contract was worth $403million. Bombardier will also maintain wayside systems (track and overhead catenary) for Line 5.

The western section has been broken up into four separate contracts: two for tunnels (Renforth to Scarlett Road, and Jane to Mount Dennis), one for the elevated guideway between Scarlett and Jane, one for stations, rail and systems for the entire west section. The first tunnel contracts were awarded in May 2021 to a consortium that included Dragados, Aecon and Ghella. The other contracts are currently progressing through bids and evaluations.

Central section
Four tunnel boring machines were ordered in July 2010 at a cost of $54million. The 10 m long, 6.5 m wide, 400 t tunnel boring machines were named Dennis, Lea, Humber, and Don. The names were inspired by Mount Dennis, Leaside, the Humber River, and the Don River, respectively.

In November 2011, ground was officially broken in Keelesdale Park by Mayor Rob Ford and Premier Dalton McGuinty. Construction for the tunnels began in August 2011, and all four tunnel boring machines completed their work in 2016, with a total of 51,825 precast concrete tunnel segments installed into 8,642 rings to line the 9.7 km stretch of twin tunnels. Work on at-grade sections commenced in the summer of 2017. In 2018, work on the Eglinton Maintenance and Storage Facility was substantially complete.

By September 2015, the deadlines for completing the central section of Line 5 began to shift, as then-Transportation Minister Steven Del Duca issued a statement saying the Crosstown would not operate until September 2021, in order "to mitigate disruption to the local community and infrastructure as much as possible." In September 2016, Bombardier Transportation (now Alstom, the vehicle supplier for the line) failed to meet the delivery deadline for the pilot vehicle, resulting in Metrolinx taking legal action to cancel the contract. This action was eventually settled, and the first Flexity Freedom vehicle was dewlivered in January 2019. Metrolinx announced that all 76 of the vehicles were delivered and run through initial testing by February 2022. The vehicle delivery did not end up becoming a factor delaying the opening date.

In 2018, Crosslinx intiated legal action against Metrolinx and sought to extend the transit line's 2021 completion date, but this was settled later that year under undisclosed terms. The Auditor General of Ontario later revealed one of the terms was paying Crosslinx an additional $237million to meet Metrolinx's 2021 deadline.

Despite the additional payment, Crosslinx informed Metrolinx in November 2019 that it expected the line not to be completed before May 6, 2022, citing complications at Eglinton, Avenue, and Mount Dennis stations. Metrolinx confirmed the delay in 2020, stating that opening would occur "well into 2022". While Metrolinx also cited complications at Eglinton station, it also blamed Crosslinx for slow / late work. Additional lawsuits were filed by Crosslinx through 2020, citing costs and delays associated with the COVID-19 pandemic and the Eglinton Station issues. The Ontario Superior Court ruled in favour of Crosslinx in 2021, and a settlement with Metrolinx and Infrastructure Ontario was reached later that year to pay the consortium an extra $325million...

