Inspectors criticised teaching and leadership at the Phoenix Academy and Lakeside Academy following visits in February, rating both schools inadequate in all areas.
Wrockwardine Wood and Sutherland academies, also run by the Telford Co-operative Multi-Academy Trust, were put in special measures earlier this week.
The trust has not commented.
Ofsted criticised the trust's lack of support to the schools and said each was now considering an alternative sponsor.
Inspectors said pupils' achievement at the Phoenix Academy had dropped since it became an academy in 2013 and their latest report rated it inadequate in all areas.
A report in 2013, before it converted, rated the secondary school as "requiring improvement", while Lakeside was rated "good" in 2012 under its former name the Lord Silkin School.
In the latest report, inspectors said the curriculum at Phoenix Academy was "inadequate", while "weak teaching" meant pupils were not sufficiently challenged and were often "disengaged and disruptive".
There was particular criticism of standards in English and maths which the watchdog said were limiting pupils' achievements in other areas.
Ofsted's report said governors, managers and teachers had developed a "culture of low expectations", while leaders had failed to act decisively to halt the decline in pupils' achievement.
There was, however, some praise for the acting head teacher. Inspectors said he had introduced a number of improvement measures and some were "beginning to have an impact".
A report on Lakeside School highlighted similar concerns, criticising teachers for not sufficiently challenging pupils and for having "over generous" predictions of their achievement.
Inspectors said many pupils, whether high achievers or those with special educational needs, were "not making the progress they should" and achievements at GCSE were well below the national average.
Governors were also criticised for not holding leaders to account, while the report said management had failed to effectively monitor either pupils or teachers.
Inspectors, did however highlight new initiatives to improve literacy which they said were "beginning to have a positive impact".
All four schools run by a Telford academy trust have been put in special measures within a week.